N,N-Diethylaniline → 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

HRID 432128

반응식

HRID 432128 반응식
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2O)[NH:4][N:3]=1.CCN(C1C=CC=CC=1)CC.O(Cl)[Cl:24]>>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[Cl:24])[NH:4][N:3]=1

참가 물질

4

반응물 3

HCID 7061N,N-DiethylanilineHCID 24646Chlorine monoxideHCID 178518058HCID 178518058, 화합물2회

생성물 1

HCID 1784783943-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

반응 조건

온도
106 °C

실험 절차

3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-ol (Intermediate A) (15.08 g, 70.5 mmol) was suspended in 189 ml of phosphous oxychloride. Diethylaniline (19 ml, 119.4 mmol) was added and the resulting reaction mixture was heated to 106° C. for 2 hours. After cooling to room temperature, the solvent was removed and the resulting amber syrup was poured to 300 ml of ice-water. 20 minutes later, the aqueous layer was extracted with diethyl ether (500 ml×4). The combined organic layer was washed, dried and evaporated to give 6.87 g of 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine as light yellow solid. 1H NMR (DMSO) 8.857 (s, 1H), 14.84 (bs, 1H); LC/MS (MH+=233).

후처리

  1. customthe resulting reaction mixture
  2. temperatureAfter cooling to room temperature
  3. customthe solvent was removed
  4. additionthe resulting amber syrup was poured to 300 ml of ice-water
  5. extraction20 minutes later, the aqueous layer was extracted with diethyl ether (500 ml×4)
  6. washThe combined organic layer was washed
  7. customdried
  8. customevaporated

출처 및 근거

ORD 기록
ord-af5b8cd11a6e48ddbdeaaa64cecd13df
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660744B1

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