Triethylamine → (R)-1-[6-Methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]-propan-2-ol

HRID 230183

반응식

HRID 230183 반응식
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]2[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:11]=[CH:12][C:3]=12.C(N(CC)CC)C.[NH2:28][CH2:29][C@@H:30]([OH:32])[CH3:31]>C1COCC1>[CH3:9][S:8][C:6]1[N:5]=[C:4]2[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:11]=[CH:12][C:3]2=[C:2]([NH:28][CH2:29][C@H:30]([OH:32])[CH3:31])[N:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 7311736(S)-(+)-1-Aminopropan-2-olHCID 866004854-Chloro-6-methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine

생성물 1

HCID 68876938(R)-1-[6-Methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]-propan-2-ol수율 107.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-Chloro-6-methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine (391 mg, 1.182 mmol) was dissolved in 5 mL of dry THF. Triethylamine (239 mg, 2.363 mmol) was added, and the reaction mixture was stirred for four hours. (S)-1-Amino-propan-2-ol (93 mg, 1.241 mmol) was then added, and the reaction mixture was stirred for 64 hours. The reaction mixture was quenched by addition to water, and was partitioned between water and ethyl acetate. The organic layer was separated, dried over MgSO4, filtered, and evaporated under reduced pressure to give (R)-1-[6-Methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]-propan-2-ol (469 mg). Mass Spec. M+H=370.

후처리

  1. stirringthe reaction mixture was stirred for 64 hours
  2. customThe reaction mixture was quenched by addition to water
  3. customwas partitioned between water and ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-d86f1e23ab0341ae9b8e4a580b21a1cb
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566708B2

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