1,1-dimethylethyl (2S)-2-(3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-ylmethyl)-1-pyrrolidinecarboxylate → 3-[(2S)-2-pyrrolidinylmethyl]-3H-[1,2,3]triazolo[4,5-d]pyrimidine

HRID 1366711노트

반응식

HRID 1366711 반응식
[N:1]1[C:9]2[CH:8]=[N:7][CH:6]=[N:5][C:4]=2[N:3]([CH2:10][C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2C(OC(C)(C)C)=O)[N:2]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH:12]1[CH2:13][CH2:14][CH2:15][C@H:11]1[CH2:10][N:3]1[C:4]2[N:5]=[CH:6][N:7]=[CH:8][C:9]=2[N:1]=[N:2]1

참가 물질

4

반응물 1

HCID 669363511,1-dimethylethyl (2S)-2-(3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-ylmethyl)-1-pyrrolidinecarboxylate

생성물 1

HCID 669365273-[(2S)-2-pyrrolidinylmethyl]-3H-[1,2,3]triazolo[4,5-d]pyrimidine수율 57%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매

실험 절차

1,1-Dimethylethyl (2S)-2-(3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-ylmethyl)-1-pyrrolidinecarboxylate (1.98 g, 6.54 mmol) was dissolved in a mixture of CH2Cl2 (10 mL) and TFA (2.5 mL) and allowed to stir at room temperature overnight. When the reaction was complete as determined by LCMS, the solution was concentrated in vacuo, and the residue was dissolved in CH2Cl2 (5 mL) and washed with 1 N aq. NaOH (30 mL). The aqueous layer was extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo to provide 3-[(2S)-2-pyrrolidinylmethyl]-3H-[1,2,3]triazolo[4,5-d]pyrimidine (758 mg, 57%). LCMS: (M+H)+: 205.1.

후처리

  1. concentrationthe solution was concentrated in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2 (5 mL)
  3. washwashed with 1 N aq. NaOH (30 mL)
  4. extractionThe aqueous layer was extracted with CH2Cl2 (3×20 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9f33368b545548d5873e31a30239eb78
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893056B2

반응 노트

불러오는 중…