CN102115476A - 2H-pyrazolo [3, 4-d] pyrimidine derivative and synthetic method thereof - Google Patents
2H-pyrazolo [3, 4-d] pyrimidine derivative and synthetic method thereof Download PDFInfo
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- CN102115476A CN102115476A CN2011100708045A CN201110070804A CN102115476A CN 102115476 A CN102115476 A CN 102115476A CN 2011100708045 A CN2011100708045 A CN 2011100708045A CN 201110070804 A CN201110070804 A CN 201110070804A CN 102115476 A CN102115476 A CN 102115476A
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Abstract
The invention belongs to the field of organic synthesis and relates to a 2H-pyrazolo [3, 4-d] pyrimidine derivative (i.e., 2-(4-substituted phenyl)-4-chloro-2H-pyrazolo [3, 4-d] pyrimidine) and a synthetic method thereof. In the general structural formula of 2-(4-substituted phenyl)-4-chloro-2H-pyrazolo [3, 4-d] pyrimidine, R refers to hydrogen, alkyl, alkoxyl, halogen, cyan, nitro, carboxyl, ester group and the like; and tetrahydrofuran is adopts as solvent, 4-substituted phenylhydrazine reacts with 4, 6-(dichloro-pyrimidine)-5-methanal under the action of triethylamine, most solvent is vaporized after reaction completion, a crude product precipitates out as a solid by adding water, the crude product filtered out is recrystallized with absolute methanol, and then isomer is removed by a column separation method to obtain corresponding 2-(4-substituted phenyl)-4-chloro-2H-pyrazolo [3, 4-d] pyrimidine. The 2H-pyrazolo [3, 4-d] pyrimidine derivative is synthesized for the first time by selecting reasonable reaction conditions.
Description
Technical field
The present invention relates to a kind of 2H-pyrazolo [3,4-d] pyrimidine derivatives is 2-(4-substituted-phenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidine and synthetic method thereof, with 4-substituted phenylhydrazines and 4,6-dichloro pyrimidine-5-formaldehyde is raw material, tetrahydrofuran (THF) is a solvent, next step reaction Synthetic 2-(4-substituted-phenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidine of room temperature.
Background technology
As the structural unit of important biomolecule molecular dna and ATP, pyrazoles and Pyrazolopyrimidine derivative thereof have wide biological activity, are the dominance structures in the new drug design, are subjected to the great attention of pharmaceutical chemists always.Develop many cancer therapy drugs based on pyrimidine derivatives compounds such as 1H-pyrazoles [3,4-d] pyrimidines at present, be widely used in multiple treatment of diseases such as tumour, inflammation, cardiovascular, asthma and nervosa clinically.For example, be used for clinical Zyloric can treat primary and secondary hyperuricemia, repeatedly outbreak or chronic gout, uratoma, the uric acid kidney is solid and urate nephropathy and the hyperuricemia of renal insufficiency is arranged, other many pyrimidine derivatives also have been proved to be anti-inflammatory and antitumous effect clinically.
2-(4-substituted-phenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidine is the effect structure that a class has certain inhibition leukemia cell growth, can be used as one of building block of chemosynthesis leukemia kinase inhibitor.The structure of this this compounds and synthetic method do not have report before this as yet.The present invention proposes the structure of 2-(4-substituted-phenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidine, wherein the substituting group on the phenyl ring comprises hydrogen, alkyl, alkoxyl group, halogen, cyano group, nitro, carboxyl, ester group.With corresponding 4-substituted phenylhydrazines and 4,6-dichloro pyrimidine-5-formaldehyde is raw material, selects synthetic this class formation that obtained of rational reaction conditions.
Summary of the invention
The present invention provides pharmaceutical intermediate 2-(4-substituted-phenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidine and synthetic method thereof in order to overcome above-mentioned deficiency of the prior art.
2-(4-substituted-phenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidine, its general structure can be expressed as follows:
;
R wherein is H, alkyl, alkoxyl group, halogen, cyano group, nitro, carboxyl or ester group etc.
This structure synthetic is having corresponding substituent 4-substituted phenylhydrazines and 4, and 6-dichloro pyrimidine-5-formaldehyde reaction directly obtains 2-(4-substituted-phenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidine.
Concrete chemical equation is:
2-(4-substituted-phenyl)-4-chloro-2H-pyrazolo [3; 4-d] preparation method of pyrimidine; carry out according to following step: the 4-substituted phenylhydrazines is dissolved in tetrahydrofuran (THF); add the acid binding agent triethylamine; stirring at room 1h; nitrogen protection slowly adds 4 down; 6-dichloro pyrimidine-5-formaldehyde at room temperature reacts; add 2 times of triethylamines after dropwising, reaction steams most of solvent after finishing, and adds water the crude product solid is separated out; earlier carry out recrystallization after leaching crude product with anhydrous methanol; adopt the isolating method of post to remove isomer again, obtain corresponding 2-(4-substituted-phenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidine.
Wherein said 4-substituted phenylhydrazines and 4,6-dichloro pyrimidine-5-formaldehyde mole ratio is 1:(0.8-1.2)
Wherein said 4-substituted phenylhydrazines and triethylamine mol ratio are 1:(1-1.5).
Advantage of the present invention
The structure of this this compounds and synthetic method do not have report before this as yet.The present invention proposes the structure of 2-(4-substituted-phenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidine, wherein the substituting group on the phenyl ring comprises hydrogen, alkyl, alkoxyl group, halogen, cyano group, nitro, carboxyl, ester group.With corresponding 4-substituted phenylhydrazines and 4,6-dichloro pyrimidine-5-formaldehyde is raw material, selects synthetic this class formation that obtained of rational reaction conditions.
Embodiment
Embodiment 1
2-phenyl-4-chloro-2H-pyrazolo [3,4-d] pyrimidines (3a)
Add the THF of 50ml, 5.0mmol hydrazinobenzene hydrochloride salt and 5.0mmol triethylamine, stirring at room 1h at the there-necked flask of 100ml; under the nitrogen protection 4 of slow Dropwise 5 .0mmol, 6-dichloro pyrimidine-5-formaldehyde is added the 11.0mmol triethylamine after dripping off; continue reaction under the room temperature, TLC follows the tracks of (developping agent V
Acetone: V
Sherwood oil=1:2), the 25h afterreaction finishes, and the underpressure distillation concentrated solvent adds 20ml water to 10ml, has a large amount of white solids to separate out, and be cooled to room temperature and filter, the filter residue recrystallizing methanol, silica gel column chromatography separates (V
Acetone: V
Sherwood oil=1:2), obtain 2-phenyl-4-chloro-2H-pyrazolo [3,4-d] pyrimidine.
Embodiment 2
2-(4-bromophenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidines (3b)
The THF that adds 60ml at the there-necked flask of 100ml; 5.0mmol 4-bromophenyl-hydrazine hydrochloride and 5.5mmol triethylamine; stirring at room 1h; slow Dropwise 5 .5mmol 4 under the nitrogen protection; 6-dichloro pyrimidine-5-formaldehyde; add the 12mmol triethylamine after dripping off, continue reaction under the room temperature, TLC follows the tracks of (developping agent V
Acetone: V
Sherwood oil=1:2), the 32h afterreaction finishes, and the underpressure distillation concentrated solvent adds 20ml water to 10ml, has a large amount of pale brown look solids to separate out, and be cooled to room temperature and filter, the filter residue recrystallizing methanol, silica gel column chromatography separates (V
Acetone: V
Sherwood oil=1:2), obtain 2-(4-bromophenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidine.
Embodiment 3
2-(4-chloro-phenyl-)-4-chloro-2H-pyrazolo [3,4-d] pyrimidines (3c)
The THF that adds 50ml at the there-necked flask of 100ml; 5.0mmol 4-chlorophenyl hydrazine hydrochloride and 6.3mmol triethylamine; stirring at room 1h; nitrogen protection slowly drips 6.0mmol 4 down; 6-dichloro pyrimidine-5-formaldehyde; add the 13mmol triethylamine after dripping off, continue reaction under the room temperature, TLC follows the tracks of (developping agent V
Acetone: V
Sherwood oil=1:2), the 28h afterreaction finishes, and the underpressure distillation concentrated solvent adds 20ml water to 10ml, has a large amount of yellow solids to separate out, and be cooled to room temperature and filter, the filter residue recrystallizing methanol, silica gel column chromatography separates (V
Acetone: V
Sherwood oil=1:2), obtain 2-(4-chlorophenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidine.
Embodiment 4
2-(4-aminomethyl phenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidines (3d)
The THF that adds 50ml at the there-necked flask of 100ml; 5.0mmol 4-procarbazine hydrochloride and 5.5mmol triethylamine; stirring at room 1h; nitrogen protection slowly drips 4.5mmol 4 down; 6-dichloro pyrimidine-5-formaldehyde; add the 12.2mmol triethylamine after dripping off, continue reaction under the room temperature, TLC follows the tracks of (developping agent V
Acetone: V
Sherwood oil=1:2), the 25h afterreaction finishes, and the underpressure distillation concentrated solvent adds 20ml water to 10ml, has a large amount of white solids to separate out, and be cooled to room temperature and filter, the filter residue recrystallizing methanol, silica gel column chromatography separates (V
Acetone: V
Sherwood oil=1:2), obtain 2-(4-aminomethyl phenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidine.
Embodiment 5
2-(4-p-methoxy-phenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidines (3e)
The THF that adds 50ml at the there-necked flask of 100ml; 5.0mmol 4-methoxyl group hydrazinobenzene hydrochloride salt and 5.8mmol triethylamine; stirring at room 1h; nitrogen protection slowly drips 4.6mmol 4 down; 6-dichloro pyrimidine-5-formaldehyde; add the 15.5mmol triethylamine after dripping off, continue reaction under the room temperature, TLC follows the tracks of (developping agent V
Acetone: V
Sherwood oil=1:2), the 20h afterreaction finishes, and the underpressure distillation concentrated solvent adds 20ml water to 10ml, has a large amount of white solids to separate out, and be cooled to room temperature and filter, the filter residue recrystallizing methanol, silica gel column chromatography separates (V
Acetone: V
Sherwood oil=1:2), obtain 2-(4-p-methoxy-phenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidine.
Embodiment 6
2-(4-nitrophenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidines (3f)
The THF that adds 60ml at the there-necked flask of 100ml; 5.0mmol 4-nitrophenyl hydrazine hydrochloride and 7.0mmol triethylamine; stirring at room 1h; slow Dropwise 5 .2mmol 4 under the nitrogen protection; 6-dichloro pyrimidine-5-formaldehyde; add the 15.5mmol triethylamine after dripping off, continue reaction under the room temperature, TLC follows the tracks of (developping agent V
Acetone: V
Sherwood oil=1:2), the 30h afterreaction finishes, and the underpressure distillation concentrated solvent adds 20ml water to 10ml, has a large amount of white solids to separate out, and be cooled to room temperature and filter, the filter residue recrystallizing methanol, silica gel column chromatography separates (V
Acetone: V
Sherwood oil=1:2), obtain 2-(4-nitrophenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidine.
Embodiment 7
2-(4-carboxyl phenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidines (3g)
The THF that adds 80ml at the there-necked flask of 100ml; 5.0mmol4-carboxyl phenylhydrazine hydrochloride and 7.5mmol triethylamine; stirring at room 1h; slow Dropwise 5 .9mmol 4 under the nitrogen protection; 6-dichloro pyrimidine-5-formaldehyde; add the 16.7mmol triethylamine after dripping off, continue reaction under the room temperature, TLC follows the tracks of (developping agent V
Acetone: V
Sherwood oil=1:2), the 28h afterreaction finishes, and the underpressure distillation concentrated solvent adds 20ml water to 10ml, has a large amount of white solids to separate out, and be cooled to room temperature and filter, the filter residue recrystallizing methanol, silica gel column chromatography separates (V
Acetone: V
Sherwood oil=1:2), obtain 2-phenyl-4-chloro-2H-pyrazolo [3,4-d] pyrimidine.
Each product physical constant and reaction yield among the table 1 embodiment 1-7
| Compound | Molecular formula | Outward appearance | m.p./ oC | Yield |
| 3a | C 11H 7ClN 4 | The white powder solid | 87.3~87.5 | 23% |
| 3b | C 11H 6BrClN 4 | Pale yellow powder shape solid | 158.5~158.7 | 25% |
| 3c | C 11H 6Cl 2N 4 | Pale yellow powder shape solid | 133.0~133.7 | 27% |
| 3d | C 12H9ClN 4 | The white powder solid | 108.9~109.3 | 24% |
| 3e | C 12H 9ClN 4O | The white powder solid | 124.1~124.6 | 26% |
| 3f | C 11H 6ClN 5O 2 | The white powder solid | 205.2~205.5 | 20% |
| 3g | C 12H 7ClN 4O 2 | The white powder solid | 225.1~225.6 | 25% |
Each product among the table 2 embodiment 1-7
1H NMR data
| Compound | 1H NMR(CDCl3,500MHz), δ |
| 3a | 7.36(t,J=7.5Hz,1H), 7.60(t,J=7.6Hz,2H),8.22(d,J=8.0Hz,2H),8.22(s,1H),8.67(s, 1H) |
| 3b | 7.68 (d, J= 8.5 Hz, 2H), 8.16(d, J = 8.5Hz 2H), 8.35(s, 1H), 8.88(s, 1H) |
| 3c | 7.50 (d, J= 8.5 Hz, 2H), 8.21 (d, J = 6.5 2H),8.22 (s, 1H), 8.66 (s, 1H) |
| 3d | 2.42 (t,3H), 7.33 (d, J=8.0Hz,2H), 8.02(d,J=8.5Hz,2H), 8.19 (s,1H), 8.64 (s,1H) |
| 3e | 3.87(t,3H),7.05(d,J=9.0Hz,2H), 8.01(d,J=9.0Hz, 2H), 8.317(s,1H), 8.845 (s, 1H) |
| 3f | 7.29(d, J =9.0 Hz, 2H), 8.01(d, J = 9.0 Hz, 2H), 8.28(s, 1H),9.25(s, 1H) |
| 3g | 7.15 (d, J= 9.0 Hz, 2H), 7.86 (d, J = 9.0 2H),8.14 (s, 1H), 8.80 (s, 1H), 11.50 (s, 1H) |
Among the table 3 embodiment 1-7 each product IR and
13C HMR data
Claims (4)
1. a 2H-pyrazolo [3,4-d] pyrimidine derivatives is characterized in that its general structure is as follows:
；
R wherein is H, alkyl, alkoxyl group, halogen, cyano group, nitro, carboxyl or ester group.
2. a kind of 2H-pyrazolo [3 according to claim 1; 4-d] synthetic method of pyrimidine derivatives; it is characterized in that carrying out: the 4-substituted phenylhydrazines is dissolved in tetrahydrofuran (THF) according to following step; add the acid binding agent triethylamine; stirring at room 1h; nitrogen protection slowly adds 4 down; 6-dichloro pyrimidine-5-formaldehyde at room temperature reacts; add 2 times of triethylamines after dropwising, reaction steams most of solvent after finishing, and adds water the crude product solid is separated out; earlier carry out recrystallization after leaching crude product with anhydrous methanol; adopt the isolating method of post to remove isomer again, obtain corresponding 2-(4-substituted-phenyl)-4-chloro-2H-pyrazolo [3,4-d] pyrimidine.
3. the synthetic method of a kind of 2H-pyrazolo according to claim 2 [3,4-d] pyrimidine derivatives is characterized in that wherein said 4-substituted phenylhydrazines and 4, and 6-dichloro pyrimidine-5-formaldehyde mole ratio is 1:0.8-1.2.
4. the synthetic method of a kind of 2H-pyrazolo according to claim 2 [3,4-d] pyrimidine derivatives is characterized in that the 4-substituted phenylhydrazines of adding when wherein said reaction is initial and the mol ratio of triethylamine are 1:1-1.5.
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Cited By (5)
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| CN105017256A (en) * | 2014-04-29 | 2015-11-04 | 浙江导明医药科技有限公司 | Polyfluorinated compound Bruton tyrosine kinase inhibitor |
| JP2018507256A (en) * | 2015-02-11 | 2018-03-15 | デウン ファーマシューティカル カンパニー リミテッド | Sodium channel blocker |
| CN113429411A (en) * | 2021-08-03 | 2021-09-24 | 韶远科技（上海)有限公司 | Preparation method of 1-alkyl-6-chloro-1H-pyrazolo [3,4-d ] pyrimidine compound |
| US11369620B2 (en) | 2015-03-19 | 2022-06-28 | Zhejiang DTRM Biopharma Co. Ltd. | Pharmaceutical compositions and their use for treatment of cancer and autoimmune diseases |
| US11622965B2 (en) | 2017-10-27 | 2023-04-11 | Zhejiang DTRM Biopharma Co. Ltd. | Methods for treating lymphoid malignancies |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105017256A (en) * | 2014-04-29 | 2015-11-04 | 浙江导明医药科技有限公司 | Polyfluorinated compound Bruton tyrosine kinase inhibitor |
| US10300066B2 (en) | 2014-04-29 | 2019-05-28 | Zhejiang DTRM Biopharma Co. Ltd. | Polyfluorinated compounds acting as bruton tyrosine kinase inhibitors |
| JP2018507256A (en) * | 2015-02-11 | 2018-03-15 | デウン ファーマシューティカル カンパニー リミテッド | Sodium channel blocker |
| US10590078B2 (en) | 2015-02-11 | 2020-03-17 | Daewoong Pharmaceutical Co., Ltd. | Sodium channel blockers |
| US11369620B2 (en) | 2015-03-19 | 2022-06-28 | Zhejiang DTRM Biopharma Co. Ltd. | Pharmaceutical compositions and their use for treatment of cancer and autoimmune diseases |
| US11622965B2 (en) | 2017-10-27 | 2023-04-11 | Zhejiang DTRM Biopharma Co. Ltd. | Methods for treating lymphoid malignancies |
| CN113429411A (en) * | 2021-08-03 | 2021-09-24 | 韶远科技（上海)有限公司 | Preparation method of 1-alkyl-6-chloro-1H-pyrazolo [3,4-d ] pyrimidine compound |
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