Ammonia → 2,6-Diamino-9-[3-(diethoxyphosphorylmethoxy)propoxy]purine

HRID 345075Notes

Reaction equation

HRID 345075 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][CH2:17][O:18][CH2:19][P:20]([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[O:21].[NH3:28]>>[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][CH2:17][O:18][CH2:19][P:20]([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[O:21])=[C:2]([NH2:28])[N:10]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 199935066-Chloro-9-[3-(diethoxyphosphorylmethoxy)propoxy]-2-formamidopurine

Product 1

HCID 199935142,6-Diamino-9-[3-(diethoxyphosphorylmethoxy)propoxy]purineYield 32%

Procedure

A solution of 6-chloro-9-[3-(diethoxyphosphorylmethoxy)propoxy]-2-formamidopurine (1.2 g, 2.85 mmol) in ethanolic ammonia (25 ml) was heated at 110° C. in an autoclave for 7.5 h then left to cool for 12 h. The reaction was then evaporated in vacuo and the residue chromatographed on silica eluting with chloroform/methanol (10:1) to give 2,6-diamino-9-[3-(diethoxyphosphorylmethoxy)propoxy]purine as a pale yellow solid (0.34 g, 32%); νmax (KBr) 3313, 3149, 1586, 1481, 1240, 1054 cm-1 ; δH [(CD3)2SO] 1.22(6H, t, J7 Hz,(CH3CH2O)2), 1.91(2H, m, CH2CH2CH2), 3.70(2H, t, J6 Hz, CH2OCH2P), 3.84(2H, d, J7.98 Hz,CH2P), 4.04(4H, m,(CH3CH2O)2), 4.31(2 H, t, J6.5 Hz, NOCH2), 5.93(2H, br.s, D2O exchangeable, NH2), 6.77(2H, br.s, D2O exchangeable, NH2), 7.94(1H, s, H-8); Found C, 41.25; H, 6.32; N, 22.65%; M+ 374.1477; C13H23N6O5P.0.2H2O requires: C, 41 31; H, 6.35; N, 22.24%; M+ 374.1468.

Workup

  1. waitthen left
  2. temperatureto cool for 12 h
  3. customThe reaction was then evaporated in vacuo
  4. customthe residue chromatographed on silica eluting with chloroform/methanol (10:1)

Sources & evidence

ORD record
ord-776ad63be7fe436b9da36f82e4dc0681
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Reaction notes

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