Sodium hydride → 4-Chloro-3-(2-chloro-phenyl)-6-methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1821594

반응식

HRID 1821594 반응식
[Cl:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]2[NH:10][N:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:3]=12.[CH3:20][Si:21]([CH3:29])([CH3:28])[CH2:22][CH2:23][O:24][CH:25](Cl)Cl.[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]2[N:10]([CH2:25][O:24][CH2:23][CH2:22][Si:21]([CH3:29])([CH3:28])[CH3:20])[N:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:3]=12

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 866110432-(Trimethylsilyl)-ethoxymethylene chlorideHCID 178503465HCID 178503465, 화합물

생성물 1

HCID 578933704-Chloro-3-(2-chloro-phenyl)-6-methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine수율 70.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-chloro-3-(2-chloro-phenyl)-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine (2.30 g, 7.39 mmol) and 2-(trimethylsilyl)-ethoxymethylene chloride (1.96 mL, 11.086 mmol) in dry DMF (40 mL) at 0° C. under nitrogen was added sodium hydride (0.354 g of 60% solids in mineral oil, 14.78 mmol). The reaction mixture was stirred for two hours and allowed to warm to room temperature during this time. The reaction mixture was partitioned between water and ethyl acetate, and the organic layer was separate, washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was chromatographed on silica (01% to 20% EtOAc in hexanes) to give 2.30 g of 4-chloro-3-(2-chloro-phenyl)-6-methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine

후처리

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customthe organic layer was separate
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on silica (01% to 20% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-d25ffac6c47043adb33dc2078e34288f
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608603B2

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