EP0169864A1 - Verfahren zur gewinnung von salzsauren salzen des 2,5,6-triam ino-4(1h)-pyrimidinons - Google Patents

Verfahren zur gewinnung von salzsauren salzen des 2,5,6-triam ino-4(1h)-pyrimidinons

Info

Publication number
EP0169864A1
EP0169864A1 EP85900657A EP85900657A EP0169864A1 EP 0169864 A1 EP0169864 A1 EP 0169864A1 EP 85900657 A EP85900657 A EP 85900657A EP 85900657 A EP85900657 A EP 85900657A EP 0169864 A1 EP0169864 A1 EP 0169864A1
Authority
EP
European Patent Office
Prior art keywords
tap
pyrimidinone
mol
reaction
isopropyl alcohol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP85900657A
Other languages
German (de)
English (en)
French (fr)
Inventor
Holger Blum
Gernot Dreesmann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of EP0169864A1 publication Critical patent/EP0169864A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/50—Three nitrogen atoms

Definitions

  • the invention relates to a method for extracting the salt.
  • TAP has Chemical Abstracts registration number 51 324 -37-9
  • DANP has Chemical Abstracts registration number 2 387-48-6.
  • TAP For chemical reactions in aqueous or aqueous / alcoholic solution, the TAP must be available as a readily soluble dihydrochloride (C.B. Storm, J. Org «Chem. 36 (1971) 3925).
  • TAP-di-HCl can be obtained by reacting TAP sulfate with aqueous barium chloride solution, the resulting solution, in addition to the foreign organic accompanying substances still contains excess barium ions, which is questionable from a physiological point of view.
  • TAP The products made from TAP are mostly natural products or important pharmaceutical components such as guanine, xanthine, folic acid and biopterin.
  • TAP sulfate dissolves only slightly in hot 2% sulfuric acid and one is forced to work with large volumes, moreover the TAP sulfate purified in this way still has to be added a second reaction stage with BaCl 2 can be converted to TAP-DiHCl.
  • the object of the invention was therefore to use TAP-Di-HCl with small amounts in a technically simple and economical manner - i.e. less than 1 mol.% - to produce foreign organic substances directly from the reduction products of the DANP with a single cleaning process.
  • reaction with hot hydrochloric acid alone can remove a considerable part of the organic impurities accompanying the TAP.
  • foreign matter contents of less than 1 mol% can only be achieved with about 20% by weight in the reaction medium after the addition of isopropyl alcohol.
  • a particular advantage of the process according to the invention is that it allows the direct separation of pure TAP-Di-HCl from the filtered reduction solution of the Raney nickel hydrogenation. Accordingly, without the loss of yield, the intermediate stage of the separation of TAP sulfate using H ⁇ SO. perform, the filtered alkaline reducing solution ⁇ g acidified to H 2 and evaporated. The resulting syrup-thick crystal slurry is then subjected to the cleaning procedure according to the invention, pure TAP-Di-HCl being obtained in about 90% yield, based on DANP.
  • reaction media were prepared by introducing hydrochloric acid gas into water / alcohol mixtures.
  • the composition of the reaction media in alcohol and hydrochloric acid is shown in the table below, the water content always making up the residual percentages to 100% by weight.
  • the crude reduction product of the DANP was then suspended in the form of the impure TAP sulfate or the TAP mono-HCl in the reaction media prepared in this way.
  • the suspensions contained about 0.2 to 0.25 grams of TAP salt per kilogram of reaction medium.
  • the batches were optionally kept under mild positive pressure at about 80 ° C. for the duration of the stated time, then cooled to below 30 ° C. and the crystals of TAP-di-HCl were washed with isopropyl alcohol. After drying in vacuo at 40 ° C, the crystals were analyzed.
  • TAP-MonoHCl 20 40 isopropanol 1 hour 80 ° C 99.2 mol% 99.6 mol%.
  • TAP sulfate 10 20 isopropanol 1 hour 80 ° C 99 mol% 98.5 mol%
  • the raw TAP sulfate used had a purity of 92% by weight elementary analysis and a purity of 103 mol% iodometric.
  • the crude TAP-MonoHCl used had a purity of 89 mol% elemental analysis and a purity of 94 mol% iodometric.
  • Example 2 18 grams of the crude TAP sulfate used in Example 1 was suspended in 310 grams of 20% hydrochloric acid. The mixture was heated to 100 ° C., and solution occurred. After * 20 minutes, the solution was cooled to 80 ° C., 200 grams of isopropanol were added and the mixture was stirred at 80 ° C. for a further 6 ⁇ minutes.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP85900657A 1984-02-01 1985-01-02 Verfahren zur gewinnung von salzsauren salzen des 2,5,6-triam ino-4(1h)-pyrimidinons Withdrawn EP0169864A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3403468 1984-02-01
DE3403468A DE3403468A1 (de) 1984-02-01 1984-02-01 Verfahren zur gewinnung von salzsauren salzen des 2,5,6-triamino-4(1h)-pyrimidinons

Publications (1)

Publication Number Publication Date
EP0169864A1 true EP0169864A1 (de) 1986-02-05

Family

ID=6226471

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85900657A Withdrawn EP0169864A1 (de) 1984-02-01 1985-01-02 Verfahren zur gewinnung von salzsauren salzen des 2,5,6-triam ino-4(1h)-pyrimidinons

Country Status (4)

Country Link
US (1) US4670561A (enrdf_load_stackoverflow)
EP (1) EP0169864A1 (enrdf_load_stackoverflow)
DE (1) DE3403468A1 (enrdf_load_stackoverflow)
WO (1) WO1985003506A1 (enrdf_load_stackoverflow)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8820732D0 (en) * 1988-09-02 1988-10-05 Specialist Printers Ltd Electroluminescent device & its manufacture
CN111763175A (zh) * 2020-07-23 2020-10-13 广州康瑞泰药业有限公司 4,6-二氯-2-(硫丙基)-5-氨基嘧啶的纯化方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2473802A (en) * 1949-06-21 Preparation of
FR955539A (enrdf_load_stackoverflow) * 1950-01-14

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8503506A1 *

Also Published As

Publication number Publication date
DE3403468C2 (enrdf_load_stackoverflow) 1988-06-23
DE3403468A1 (de) 1985-08-08
WO1985003506A1 (en) 1985-08-15
US4670561A (en) 1987-06-02

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