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

HRID 1836272ノート

反応式

HRID 1836272 の反応式
[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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c5d59affbbc44a0a8d6e1ed24fd07c39
出典データセット
uspto-grants-2004_08
特許番号
US06777395B2

反応ノート

読み込み中…