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

HRID 2293927Notes

Reaction equation

[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

Participants

Conditions

Temperature: 25 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-7ab93b45ff8c470a94f5908ff98ed6d3
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05688778

Reaction notes

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