Ammonia → 2,6-Diamino-9-[2-(diethoxyphosphorylmethoxy)ethoxy]purine

HRID 6262Notes

Reaction equation

HRID 6262 reaction equation
Cl[C:2]1[N:10]=[C:9]([NH:11]C=O)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[O:14][CH2:15][CH2:16][O:17][CH2:18][P:19]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:20].[NH3:27]>C(O)C>[NH2:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][N:6]2[O:14][CH2:15][CH2:16][O:17][CH2:18][P:19]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:20])=[C:2]([NH2:27])[N:10]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 148620676-Chloro-9-[2-(diethoxyphosphorylmethoxy)ethoxy]-2-formamidopurine

Product 1

HCID 197951932,6-Diamino-9-[2-(diethoxyphosphorylmethoxy)ethoxy]purineYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-chloro-9-[2-(diethoxyphosphorylmethoxy)ethoxy]-2-formamidopurine (0.80 g, 1.96 mmol) in ethanol (10 ml) saturated with ammonia gas was heated in a sealed steel vessel at 110° C. for 51/2 hours. The reaction mixture was cooled to ambient temperature, evaporated to dryness and the residue chromatographed on silica gel (eluted with dichloromethane:methanol 90:10) to give the title compound (0.25 g, 35%), m.p. 139°-141° (acetonitrile). UV: νmax (EtOH) 256 (ε8,200), 280 (ε10,200)nm:

Workup

  1. customevaporated to dryness
  2. customthe residue chromatographed on silica gel (eluted with dichloromethane:methanol 90:10)

Sources & evidence

ORD record
ord-a41c8a765ab1473ab14b8ae1cb18f13d
Source dataset
uspto-grants-1993_09
Patent number
US05247085

Reaction notes

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