Ammonia → 2,6-Diamino-9-[1-(diethoxyphosphorylmethoxy)-3-hydroxyprop-2-oxy]purine

HRID 345082Notes

Reaction equation

HRID 345082 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][CH:15]([CH2:27][OH:28])[CH2:16][O:17][CH2:18][P:19]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:20].[NH3:29]>>[NH2:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][N:6]2[O:14][CH:15]([CH2:27][OH:28])[CH2:16][O:17][CH2:18][P:19]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:20])=[C:2]([NH2:29])[N:10]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 199934976-Chloro-9-[1-(diethoxyphosphorylmethoxy)-3-hydroxyprop-2-oxy]-2-formamidopurine

Product 1

HCID 199935472,6-Diamino-9-[1-(diethoxyphosphorylmethoxy)-3-hydroxyprop-2-oxy]purineYield 28%

Procedure

A solution of 6-chloro-9-[1-(diethoxyphosphorylmethoxy)-3-hydroxyprop-2-oxy]-2-formamidopurine (400 mg, 0.91 mmol) in saturated ethanolic ammonia (20 ml) was placed in an autoclave and kept at 110° C. for 5 h. After cooling, the solvent was evaporated in vacuo and the residue chromatographed on silica, eluting with chloroform-methanol 10:1, affording 2,6-diamino-9-[1-(diethoxyphosphorylmethoxy)-3-hydroxyprop-2-oxy]purine (100 mg, 28%) as an oil. νmax (CHCl3) 3500, 3400, 1620 and 1600 cm-1 ; δH [(CD3)2SO] 1.24, (6H, t, J7.1 Hz, 2×CH2CH3), 3.58 (2H, m, CH2OH), 3.80 (2H, d, J5.0 Hz, CH2OCH2P), 3.92 (2H, d, J8.2 Hz, CH2P), 4.05 (4H,m,2×CH 2 CH3), 4.39 (1H, t, J5.0 Hz, CHON), 5.35 (1H, br.s, D2O exchangeable, OH), 6.00 (2H br.s, D2O exchangeable, NH2), 6.87 (2H, br.s, D2O exchangeable, NH2), 7.87 (1H, s, H-8); m/z (FAB+ve Ion), 391 (MH+).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated in vacuo
  3. customthe residue chromatographed on silica
  4. washeluting with chloroform-methanol 10:1

Sources & evidence

ORD record
ord-89ec97d98454434ca419a60a22d89b6d
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Reaction notes

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