1-(3,5-dimethylphenyl)-1H,4H,5H-pyrazolo[3,4-d]pyrimidin-4-one → 4-chloro-1-(3,5-dimethylphenyl)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1801687

반응식

HRID 1801687 반응식
O(Cl)[Cl:2].[P+5].[CH3:5][C:6]1[CH:7]=[C:8]([N:13]2[C:17]3[N:18]=[CH:19][NH:20][C:21](=O)[C:16]=3[CH:15]=[N:14]2)[CH:9]=[C:10]([CH3:12])[CH:11]=1>C(Cl)(Cl)Cl>[Cl:2][C:21]1[N:20]=[CH:19][N:18]=[C:17]2[N:13]([C:8]3[CH:7]=[C:6]([CH3:5])[CH:11]=[C:10]([CH3:12])[CH:9]=3)[N:14]=[CH:15][C:16]=12

참가 물질

4

반응물 2

HCID 1355447751-(3,5-dimethylphenyl)-1H,4H,5H-pyrazolo[3,4-d]pyrimidin-4-oneHCID 178479711HCID 178479711, 화합물

생성물 1

HCID 49621194-chloro-1-(3,5-dimethylphenyl)-1H-pyrazolo[3,4-d]pyrimidine수율 86.6%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

반응 조건

온도
106.5 °C

실험 절차

650.0 g of Phosphorus (V) oxychloride (POCl3) was charged into a 2.0 L 4 necked round bottom flask connected to a mechanical stirrer, thermo meter socket, and condenser under nitrogen atmosphere. 60.0 g (0.25 mol) of 1-(3,5-Dimethyl-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidine-4-one (Compound No. 78) was charged. Reaction mass temperature was raised to reflux (105-108° C.). Maintained the mass temperature at reflux for 8-9 hour's. Reaction mass temperature was cooled to 25-30° C. and 600.0 ml of chloroform was charged. Maintained the mass temperature at 25-30° C. for 30-45 min. 2.0 kg's of crushed ice was charged into a 5.0 L 4 necked round bottom flask connect to a mechanical stirrer, thermo meter socket, and condenser. Reaction mass was added slowly at maintaining the mass temperature below 10° C. Maintained the mass temperature at 0-10° C. for 30-45 min. Mass temperature was raised to 25-30° C. 600.0 ml of Chloroform was charged. Maintained the mass temperature at 25-30° C. for 30-45 min and settled the mass for 20-30 min. Separated the bottom organic layer. Organic layer was dried with sodium sulphate upto obtaining the moisture content is not more than 0.20% w/v. 15.0 g of carbon was charged. Mass temperature was raised to 45-50° C. Maintained the mass temperature at 45-50° C. for 30-45 min. Carbon and sodium sulphate was filtered through hyflow bed and bed was washed with 300.0 ml of chloroform. Filtrate was collected into a flask. Chloroform was distilled completely under vacuum at mass temperature not crossing 60° C. Finally applied high vacuum to complete remove the traces of chloroform at mass temperature not crossing 60° C. Mass temperature was cooled to 25-30° C. and release the vacuum. 250.0 ml of isopropyl ether was charged. Maintained the mass temperature at 25-30° C. for 45-60 min. Solid was filtered and the solid was washed with 50.0 ml of isopropyl ether. Compound was dried under vacuum at 55-60° C. Dry weight of the compound: 56.0 g (yield 86.6%).

후처리

  1. customconnected to a mechanical stirrer
  2. addition78) was charged
  3. customReaction mass temperature
  4. temperaturewas raised
  5. temperatureMaintained the mass temperature
  6. temperatureat reflux for 8-9 hour's
  7. customReaction mass temperature
  8. temperaturewas cooled to 25-30° C.
  9. temperatureMaintained the mass temperature at 25-30° C. for 30-45 min
  10. customconnect to a mechanical stirrer
  11. customReaction mass
  12. additionwas added slowly
  13. temperatureat maintaining the mass temperature below 10° C
  14. temperatureMaintained the mass temperature at 0-10° C. for 30-45 min
  15. temperatureMass temperature was raised to 25-30° C
  16. temperatureMaintained the mass temperature at 25-30° C. for 30-45 min
  17. customfor 20-30 min
  18. customSeparated the bottom organic layer
  19. dry with materialOrganic layer was dried with sodium sulphate
  20. customupto obtaining the moisture content
  21. addition15.0 g of carbon was charged
  22. temperatureMass temperature was raised to 45-50° C
  23. temperatureMaintained the mass temperature at 45-50° C. for 30-45 min
  24. filtrationCarbon and sodium sulphate was filtered through hyflow bed and bed
  25. washwas washed with 300.0 ml of chloroform
  26. customFiltrate was collected into a flask
  27. distillationChloroform was distilled completely under vacuum at mass temperature not
  28. customcrossing 60° C
  29. customFinally applied high vacuum to complete remove the traces of chloroform at mass temperature not
  30. customcrossing 60° C
  31. temperatureMass temperature was cooled to 25-30° C.
  32. addition250.0 ml of isopropyl ether was charged
  33. temperatureMaintained the mass temperature at 25-30° C. for 45-60 min
  34. filtrationSolid was filtered
  35. washthe solid was washed with 50.0 ml of isopropyl ether
  36. customCompound was dried under vacuum at 55-60° C
  37. customDry weight of the compound

출처 및 근거

ORD 기록
ord-94596884083c4cf0a5e0cda7bffadd8e
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349847B2

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