CN117946133A - 5- (4-Amino-1, 2, 5-oxadiazole-3-yl) [1,2,5] oxadiazole [3,4-d ] pyrimidine-7-amine and preparation method thereof - Google Patents
5- (4-Amino-1, 2, 5-oxadiazole-3-yl) [1,2,5] oxadiazole [3,4-d ] pyrimidine-7-amine and preparation method thereof Download PDFInfo
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- CN117946133A CN117946133A CN202410017503.3A CN202410017503A CN117946133A CN 117946133 A CN117946133 A CN 117946133A CN 202410017503 A CN202410017503 A CN 202410017503A CN 117946133 A CN117946133 A CN 117946133A
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- -1 5- (4-Amino-1, 2, 5-oxadiazole-3-yl) [1,2,5] oxadiazole Chemical compound 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 63
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000003756 stirring Methods 0.000 claims abstract description 26
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 239000000243 solution Substances 0.000 claims abstract description 21
- SJAYVHFNURJLAG-UHFFFAOYSA-N 4-amino-1,2,5-oxadiazole-3-carbonitrile Chemical compound NC1=NON=C1C#N SJAYVHFNURJLAG-UHFFFAOYSA-N 0.000 claims abstract description 19
- GIBOQBRSJOGEJG-UHFFFAOYSA-N [1,2,5]oxadiazolo[3,4-d]pyrimidin-7-amine Chemical compound NC1=NC=NC2=NON=C12 GIBOQBRSJOGEJG-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 16
- 239000008367 deionised water Substances 0.000 claims abstract description 10
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000011259 mixed solution Substances 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 4
- 238000001914 filtration Methods 0.000 claims abstract description 4
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 abstract description 4
- 230000035484 reaction time Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000004904 shortening Methods 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
The invention discloses 5- (4-amino-1, 2, 5-oxadiazole-3-yl) [1,2,5] oxadiazole [3,4-d ] pyrimidine-7-amine and a preparation method thereof, and relates to the technical field of organic synthesis. A process for the preparation of 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidin-7-amine comprising the following preparation steps: s1, dissolving 3-cyano-4-amino furazan in acetonitrile to obtain a mixed solution, stirring and adding a methanol solution of sodium methoxide into the mixed solution to obtain a reaction solution; s2, stirring the reaction solution at room temperature, then adding methanol, continuing stirring, S3, removing the solvent under reduced pressure after the reaction is finished, dispersing the residue in deionized water under intense stirring, filtering, and drying to obtain 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazol [3,4-d ] pyrimidine-7-amine. The preparation method of the 5- (4-amino-1, 2, 5-oxadiazole-3-yl) [1,2,5] oxadiazole [3,4-d ] pyrimidine-7-amine has the advantages of avoiding high temperature and long-time heating, greatly shortening the reaction time, greatly improving the yield and having engineering application prospects.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a preparation method of 5- (4-amino-1, 2, 5-oxadiazole-3-yl) [1,2,5] oxadiazole [3,4-d ] pyrimidine-7-amine.
Background
5- (4-Amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidin-7-amine is an energetic compound intermediate (CHEMISTRY OFHETEROCYCLIC COMPOUNDS 2017,53,760-778) synthesized in 2017 by the Lawrence Lifromo national laboratory in the U.S. The 5- (4-amino-1, 2, 5-oxadiazole-3-yl) [1,2,5] oxadiazole [3,4-d ] pyrimidine-7-amine not only can be used as an intermediate of an energetic compound, but also has a decomposition temperature of more than 300 ℃, is a potential chemical raw material or drug intermediate, and has wide application prospect.
At present, two methods exist for synthesizing 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidine-7-amine, wherein one method is to heat 3-cyano-4-amino furazan serving as a raw material in pyridine and anisole for 20 hours at 150 ℃. The reaction mixture was cooled to room temperature, the precipitate was filtered off, washed with acetone and dried to give a yield of 5%; the second method is to take 3-cyano-4-amino furazan and 3-amidoxime-4-amino furazan as raw materials, heat the raw materials in pyridine and anisole at 150 ℃ for 14 hours, and the yield can be improved to 50%. The yields of both processes are relatively low and the reaction requires high temperatures and long heating times. Therefore, the existing reaction route has high risk and low yield, and a new synthesis method of 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazol [3,4-d ] pyrimidine-7-amine needs to be developed.
Disclosure of Invention
The invention aims to provide 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidine-7-amine and a preparation method thereof, wherein 3-cyano-4-amino furazan is used as a raw material, and 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidine-7-amine is prepared in a one-step reaction with high yield.
In order to achieve the above object, the present invention provides a method for preparing 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidine-7-amine, comprising the following steps:
s1, dissolving 3-cyano-4-amino furazan in acetonitrile to obtain a mixed solution, stirring and adding a methanol solution of sodium methoxide into the mixed solution to obtain a reaction solution;
S2, stirring the reaction solution at room temperature, then adding methanol, and continuing stirring.
S3, removing the solvent under reduced pressure after the reaction is finished, dispersing the residue in deionized water under vigorous stirring, filtering, and drying to obtain 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazol [3,4-d ] pyrimidine-7-amine.
Preferably, the dosage ratio of 3-cyano-4-aminofurazan to acetonitrile in the step S1 is 1mmol:1.5-3mL.
Preferably, the concentration of the methanolic sodium methoxide solution in step S1 is 0.5M.
Preferably, the dosage ratio of the methanol solution of sodium methoxide to 3-cyano-4-amino furazan in the step S1 is 1mL:12-20mmol.
Preferably, the reaction temperature of the step S1 is 0-35 ℃.
Preferably, in the step S2, the volume ratio of the methanol addition amount to the acetonitrile use amount in the step S1 is 0.5-2mL:1mL, the first stirring time is 15min, and the second stirring time is 5min.
Preferably, in the step S3, the mass ratio of the deionized water to the raw material 3-cyano-4-amino furazan is 10-20g to 1g.
The invention also provides 5- (4-amino-1, 2, 5-oxadiazole-3-yl) [1,2,5] oxadiazole [3,4-d ] pyrimidine-7-amine prepared by the preparation method.
Therefore, the preparation method of the 5- (4-amino-1, 2, 5-oxadiazole-3-yl) [1,2,5] oxadiazole [3,4-d ] pyrimidine-7-amine has the following beneficial effects:
(1) The novel preparation method of the 5- (4-amino-1, 2, 5-oxadiazole-3-yl) [1,2,5] oxadiazole [3,4-d ] pyrimidine-7-amine has the advantages of one step, normal temperature and normal pressure, high reaction speed, avoidance of high temperature and long-time heating, greatly shortened reaction time and easiness in engineering amplification compared with the synthesis route in the prior art.
(2) The highest yield of the novel preparation method of the 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidine-7-amine is close to 90 percent, which is obviously higher than that of the prior art.
The technical scheme of the invention is further described in detail through the drawings and the embodiments.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of example 1 of a preparation method of 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidine-7-amine;
FIG. 2 is a nuclear magnetic resonance spectrum of example 1 of a method for preparing 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidin-7-amine according to the invention;
FIG. 3 is an infrared spectrum of example 1 of a preparation method of 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidine-7-amine;
FIG. 4 is a single crystal structure diagram of example 1 of a process for preparing 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidin-7-amine according to the invention;
FIG. 5 is a unit cell stacking diagram of example 1 of a process for preparing 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidin-7-amine of the invention.
Detailed Description
The technical scheme of the invention is further described below through the attached drawings and the embodiments.
The invention provides a preparation method of 5- (4-amino-1, 2, 5-oxadiazole-3-yl) [1,2,5] oxadiazole [3,4-d ] pyrimidine-7-amine, which comprises the following preparation steps:
S1.0-35 ℃, dissolving 3-cyano-4-amino furazan in acetonitrile to obtain a mixed solution, stirring and adding a methanol solution with the concentration of 0.5M sodium methoxide into the mixed solution to obtain a reaction solution, wherein the dosage ratio of 3-cyano-4-amino furazan to acetonitrile is 1mmol:1.5-3mL; the dosage ratio of the methanol solution of sodium methoxide to 3-cyano-4-amino furazan is 1mL:12-20mmol.
S2, stirring the reaction solution at room temperature for 15min, then adding methanol, and continuing stirring for 5min, wherein the volume ratio of the addition amount of the methanol to the use amount of acetonitrile in the step S1 is 0.5-2mL:1mL.
S3, removing the solvent under reduced pressure after the reaction is finished, dispersing the residue in deionized water under vigorous stirring, filtering, and drying to obtain 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidine-7-amine; the mass ratio of the dosage of deionized water to the raw material 3-cyano-4-amino furazan is 10-20g to 1g.
The invention also provides 5- (4-amino-1, 2, 5-oxadiazole-3-yl) [1,2,5] oxadiazole [3,4-d ] pyrimidine-7-amine prepared by the preparation method.
Example 1:
1.2mL of a 0.5M sodium methoxide in methanol was added dropwise to a stirred solution of 3-cyano-4-aminofurazan (2.0 g,18.2 mmol) in acetonitrile (40 mL) at room temperature of 25 ℃. The reaction was stirred at room temperature for 15min, then 40mL of methanol was added and stirring was continued for 5min. After the reaction was completed, the solvent was removed under reduced pressure, and the residue was dispersed in 30mL of deionized water with vigorous stirring, filtered, and dried to give 1.79g of 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidin-7-amine with a yield of 89.5%.
Example 2:
1mL of a 0.5M sodium methoxide in methanol was added dropwise to a stirred solution of 3-cyano-4-aminofurazan (2.0 g,18.2 mmol) in acetonitrile (30 mL) at room temperature of 5 ℃. The reaction was stirred at room temperature for 15min, then 15mL of methanol was added and stirring was continued for 5min. After the reaction was completed, the solvent was removed under reduced pressure, and the residue was dispersed in 20mL of deionized water with vigorous stirring, filtered, and dried to give 1.65g of 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidin-7-amine with a yield of 82.5%.
Example 3:
1.5mL of a 0.5M sodium methoxide in methanol was added dropwise to a stirred solution of 3-cyano-4-aminofurazan (2.0 g,18.2 mmol) in acetonitrile (50 mL) at 35℃at room temperature. The reaction was stirred at room temperature for 15min, then 80mL of methanol was added and stirring was continued for 5min. After the reaction was completed, the solvent was removed under reduced pressure, and the residue was dispersed in 40mL of deionized water with vigorous stirring, filtered, and dried to give 1.76g of 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidin-7-amine with a yield of 88%.
The 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidin-7-amine obtained in examples 1 to 3 was dissolved in methanol and slowly volatilized at room temperature to obtain a single crystal thereof, wherein the single crystal was subjected to an X-ray single crystal diffraction test on the sample culture described in example 1, the crystal structure thereof is shown in fig. 4 and 5, and the unit cell parameters thereof are as follows:
And (3) crystal system: monoclinic system;
Dot group: p2 1/n;
Unit cell parameters: α＝90°，β＝100.397(11)°，γ＝90°；
unit cell volume:
Z＝4；
density: 1.783 g.cm -3 (170K).
Characterization of 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidin-7-amine obtained in examples 1 to 3 was performed, the spectrum data were consistent, the analysis results of the samples described in example 1 were given below, and the results were consistent with the characterization data reported in the literature.
Nuclear magnetic hydrogen spectrogram shown in FIG. 1, 1H NMR(500MHz,DMSO-d6): delta 9.87,9.71,6.84ppm.
Nuclear magnetic carbon spectra, 13C NMR(DMSO-d6 as shown in FIG. 2): delta 160.10,159.28,156.52,155.72,144.14,136.37ppm.
As shown in fig. 3, IR (ATR):3618,3465,3423,3355,3087,2017,1680,1619,1599,1573,1521,1488,1470,1426,1411,1378,1208,1191,1127,1022,1009,940,874,789,775,747,718,688,680,662,654,622,601,591,568,556,540cm-1.
Elemental analysis C 6H4N8O2 (220.15): calculated (found) C32.73 (32.69), H1.83 (1.89), N50.90 (49.96).
Therefore, the invention adopts the 5- (4-amino-1, 2, 5-oxadiazole-3-yl) [1,2,5] oxadiazole [3,4-d ] pyrimidine-7-amine and the preparation method thereof, the method avoids high temperature and long-time heating, the reaction time is greatly shortened, the yield is greatly improved, and the invention has engineering application prospect.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present invention and not for limiting it, and although the present invention has been described in detail with reference to the preferred embodiments, it will be understood by those skilled in the art that: the technical scheme of the invention can be modified or replaced by the same, and the modified technical scheme cannot deviate from the spirit and scope of the technical scheme of the invention.
Claims (8)
1. A process for the preparation of 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidin-7-amine comprising the steps of:
s1, dissolving 3-cyano-4-amino furazan in acetonitrile to obtain a mixed solution, stirring and adding a methanol solution of sodium methoxide into the mixed solution to obtain a reaction solution;
S2, stirring the reaction solution at room temperature, then adding methanol, and continuing stirring;
S3, removing the solvent under reduced pressure after the reaction is finished, dispersing the residue in deionized water under vigorous stirring, filtering, and drying to obtain 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazol [3,4-d ] pyrimidine-7-amine.
2. A process for the preparation of 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidin-7-amine according to claim 1, characterized in that: the dosage ratio of the 3-cyano-4-amino furazan to the acetonitrile in the step S1 is 1mmol:1.5-3mL.
3. A process for the preparation of 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidin-7-amine according to claim 2, characterized in that: the concentration of the methanolic solution of sodium methoxide in the step S1 is 0.5M.
4. A process for the preparation of 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidin-7-amine according to claim 3, characterized in that: the dosage ratio of the methanol solution of sodium methoxide to 3-cyano-4-amino furazan in the step S1 is 1mL:12-20mmol.
5. A process for the preparation of 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidin-7-amine according to claim 2, characterized in that: the reaction temperature of the step S1 is 0-35 ℃.
6. A process for the preparation of 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidin-7-amine according to claim 3, characterized in that: in the step S2, the volume ratio of the methanol addition amount to the acetonitrile use amount in the step S1 is 0.5-2mL:1mL, the first stirring time is 15min, and the second stirring time is 5min.
7. The process for the preparation of 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidin-7-amine according to claim 4, characterized by: in the step S3, the mass ratio of the dosage of deionized water to the raw material 3-cyano-4-amino furazan is 10-20g to 1g.
8. 5- (4-Amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidin-7-amine prepared by the method of preparing 5- (4-amino-1, 2, 5-oxadiazol-3-yl) [1,2,5] oxadiazolo [3,4-d ] pyrimidin-7-amine according to any one of claims 1-7.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4220772A (en) * | 1978-07-21 | 1980-09-02 | Hoffmann-La Roche Inc. | Process for the preparation of oxadiazolopyrimidine derivatives |
| US4360521A (en) * | 1980-12-19 | 1982-11-23 | Hoffmann-La Roche Inc. | 7[3,6-Dihydro-1(2H)-pyridyl]-2-oxo-2H-[1,2,4]oxadiazolo[2,3-c]pyrimidine-5-carbamate compounds |
| US5382585A (en) * | 1992-06-10 | 1995-01-17 | Cassella Ag | Pyrimidofuroxans, their preparation and their use |
| US20080269236A1 (en) * | 2006-12-12 | 2008-10-30 | Abbott Laboratories | Novel 1,2,4 Oxadiazole Compounds and Methods of Use Thereof |
| CN111662296A (en) * | 2020-06-02 | 2020-09-15 | 山东大学 | Hydroxamic acid derivative containing pyrazolopyrimidine and preparation method and application thereof |
| KR20220130412A (en) * | 2021-03-18 | 2022-09-27 | 국방과학연구소 | Method for preparing salt derivatives of 4-nitramino-3-(5-dinitromethyl-1,2,4-oxadiazolyl)-furazanate(ndnf), salt derivatives of 4-nitramino-3-(5-dinitromethyl-1,2,4-oxadiazolyl)-furazanate thereby |
-
2024
- 2024-01-05 CN CN202410017503.3A patent/CN117946133B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4220772A (en) * | 1978-07-21 | 1980-09-02 | Hoffmann-La Roche Inc. | Process for the preparation of oxadiazolopyrimidine derivatives |
| US4360521A (en) * | 1980-12-19 | 1982-11-23 | Hoffmann-La Roche Inc. | 7[3,6-Dihydro-1(2H)-pyridyl]-2-oxo-2H-[1,2,4]oxadiazolo[2,3-c]pyrimidine-5-carbamate compounds |
| US5382585A (en) * | 1992-06-10 | 1995-01-17 | Cassella Ag | Pyrimidofuroxans, their preparation and their use |
| US20080269236A1 (en) * | 2006-12-12 | 2008-10-30 | Abbott Laboratories | Novel 1,2,4 Oxadiazole Compounds and Methods of Use Thereof |
| CN111662296A (en) * | 2020-06-02 | 2020-09-15 | 山东大学 | Hydroxamic acid derivative containing pyrazolopyrimidine and preparation method and application thereof |
| KR20220130412A (en) * | 2021-03-18 | 2022-09-27 | 국방과학연구소 | Method for preparing salt derivatives of 4-nitramino-3-(5-dinitromethyl-1,2,4-oxadiazolyl)-furazanate(ndnf), salt derivatives of 4-nitramino-3-(5-dinitromethyl-1,2,4-oxadiazolyl)-furazanate thereby |
Non-Patent Citations (3)
| Title |
|---|
| D. KIKELJ: "Product Class 13: Quinazolines", 《SCIENCE OF SYNTHESIS》, vol. 16, 31 December 2004 (2004-12-31), pages 573 - 749, XP001199770 * |
| PHILIP F. PAGORIA ET AL.: "Synthesis and characterization of multicyclic oxadiazoles and 1-hydroxytetrazoles as energetic materials", 《CHEMISTRY OF HETEROCYCLIC COMPOUNDS》, vol. 53, no. 6, 31 December 2017 (2017-12-31), pages 761 * |
| VAN MUIJLWIJK-KOEZEN ET AL.: "Isoquinoline and Quinazoline Urea Analogues as Antagonists for the Human Adenosine A3 Receptor", 《JOURNAL OF MEDICINAL CHEMISTRY》, vol. 43, no. 11, 11 May 2000 (2000-05-11), pages 2229 * |
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