Sodium hydride → 2-Amino-6-chloro-9-[(diethylphosphonomethoxy)methoxymethyl]purine

HRID 1552

反応式

HRID 1552 の反応式
[H-].[Na+].[NH2:3][C:4]1[N:12]=[C:11]2[C:7]([NH:8][CH:9]=[N:10]2)=[C:6]([Cl:13])[N:5]=1.Cl[CH2:15][O:16][CH2:17][O:18][CH2:19][P:20]([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[O:21]>CN(C=O)C>[NH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[CH2:15][O:16][CH2:17][O:18][CH2:19][P:20]([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[O:21])=[C:6]([Cl:13])[N:5]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 53603492-Amino-6-chloropurineHCID 14843539Chloromethoxy(diethylphosphonomethoxy)methane

生成物 1

HCID 148435402-Amino-6-chloro-9-[(diethylphosphonomethoxy)methoxymethyl]purine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
25 °C

実験手順

To a suspension of 60% sodium hydride in mineral oil (1.4 g, 34.5 mmol) in DMF (100 mL) was added 2-amino-6-chloropurine (5.78 g, 34.2 mmol) and the mixture was stirred for 1 hr at 25° C. To the resulting yellow solution was added dropwise a solution of above chloromethoxy(diethylphosphonomethoxy)methane in DMF (20 mL) under nitrogen. After stirring 15 hr at 25° C., volatiles were removed in vacuo. The residual oil was suspended in ethyl acetate (100 mL), washed with water (30 mL), brine and dried (MgSO4). The solvent was removed under reduced pressure, and the residual oil was chromatographed on silica gel using CH2Cl2 /3% MeOH as eluent to give the title compound as a colorless oil: yield 3.0 g (23%).

後処理

  1. stirringAfter stirring 15 hr at 25° C.
  2. customvolatiles were removed in vacuo
  3. washwashed with water (30 mL), brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed under reduced pressure
  6. customthe residual oil was chromatographed on silica gel

出典と根拠

ORDレコード
ord-77276d898fd0423db0141ad034a6f470
出典データセット
uspto-grants-1998_03
特許番号
US05726174

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