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

HRID 1552

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HRID 1552 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
25 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-77276d898fd0423db0141ad034a6f470
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726174

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