Boron Trichloride → (2R,3R,4R,5R)-2-(4-aminopyrazolo[3,4-d]pyrimidin-1-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diol

HRID 1270294노트

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HRID 1270294 반응식
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@@H:11]3[O:26][C@H:25]([CH2:27][O:28]CC4C=CC(Cl)=CC=4Cl)[C@@H:14]([O:15]CC4C=CC(Cl)=CC=4Cl)[C@@:12]3([CH3:38])[OH:13])[N:9]=[CH:10][C:3]=12.B(Cl)(Cl)Cl>ClCCl>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@@H:11]3[O:26][C@H:25]([CH2:27][OH:28])[C@@H:14]([OH:15])[C@@:12]3([CH3:38])[OH:13])[N:9]=[CH:10][C:3]=12

참가 물질

4

반응물 2

HCID 25135Boron TrichlorideHCID 112963434-Amino-1-[3,5-bis-o-(2,4-dichlorophenylmethyl)-2-c-methyl-beta-d-ribofuranosyl]-1h-pyrazolo[3,4-d]pyrimidine

생성물 1

HCID 3011894(2R,3R,4R,5R)-2-(4-aminopyrazolo[3,4-d]pyrimidin-1-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diol수율 64.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-78 °C

실험 절차

To a solution of the compound from Step A (0.20 g, 0.33 mmol) in dichloromethane (10 mL) at −78° C. was added boron trichloride (1M in dichloromethane) (3 mL, 3 mmol) dropwise. The mixture was stirred at −78° C. for 0.5 h, then at −45° C. to −30° C. for 2 h. The reaction was quenched by addition of sodium acetate (1.0 g) and methanol (10 mL). The solution was evaporated and the residue was purified by flash chromatography over silica gel using CH2Cl2 and CH2Cl2/MeOH (95:5–90:10) gradient as the eluent to furnish the desired compound (60 mg) as a solid, which was recrystallized from methanol and acetonitrile to give the title compound as an off-white solid (40 mg).

후처리

  1. waitat −45° C. to −30° C. for 2 h
  2. customThe reaction was quenched by addition of sodium acetate (1.0 g) and methanol (10 mL)
  3. customThe solution was evaporated
  4. customthe residue was purified by flash chromatography over silica gel

출처 및 근거

ORD 기록
ord-19fe63e7cca244f19c33f18924aa23e9
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07202224B2

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