Ammonia → 6-Chloro-9-[3-(diethoxyphosphoryl)propoxy]-2-formamidopurine

HRID 373876Notes

Reaction equation

HRID 373876 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][CH:9]=O)=[C:6]([NH:11][O:12][CH2:13][CH2:14][CH2:15][P:16]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17])[N:5]=[C:4]([NH:24][CH:25]=[O:26])[N:3]=1.N>C(OC(OCC)OCC)(=O)C.CO>[Cl:1][C:2]1[N:3]=[C:4]([NH:24][CH:25]=[O:26])[N:5]=[C:6]2[C:7]=1[N:8]=[CH:9][N:11]2[O:12][CH2:13][CH2:14][CH2:15][P:16]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 198086004-Chloro-6-[[3-(diethoxyphosphoryl)propoxy]amino]-2,5-diformamidopyrimidine

Product 1

HCID 198086236-Chloro-9-[3-(diethoxyphosphoryl)propoxy]-2-formamidopurine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 84166Methanol, 1,1-diethoxy-, 1-acetateSolvent

Procedure

A solution of 4-chloro-6-[[3-(diethoxyphosphoryl)-propoxy]amino]-2,5-diformamidopyrimidine (1.1 g, 2.7 mmol) in diethoxymethyl acetate (15 ml) was heated at 120° C. for 2 hours. The solution was then cooled, evaporated to dryness under reduced pressure and the residue obtained dissolved in methanol (10 ml) and 880 ammonia (1 ml). After standing at ambient temperature for 1 hr, the solvent was removed. The residue was chromatographed on silica gel (dichloromethane-methanol (98:2) as eluant) to give the title compound as a colorless oil which crystallised on standing, mp. 121°-124°, (1.01 g, 95%). IR: υmax (KBr) 1700, 1618, 1577, 1506, 1439, 1405, 1383, 1328, 1259, 1242, 1226, 1165, 1052, 1024, 972, 918 cm-1. 1H NMR: δH ((CD3)2SO) 1.21 (6H, t, J=7Hz, (O--CH2CH3)2), 1.75-2.1 (4H, m, CH2CH2P), 3.99 (4H, m, (OCH2CH3)2), 4.47 (2H, t, J=6Hz, N--OCH2), 8.83 (1Y, s, H--8), 9.37 (1H, s, CHO), 11.30 (1H, bs, D2O exchangeable, NHCHO). Found: C, 39.82; H, 4.96; N, 17.65%. C13H19N5O5ClP requires: C, 39.85; H, 4.89; N, 17.88%. m/z: C13H20N5O5PCl requires: 392.0890. Observed: 392.0888 (MH+).

Workup

  1. temperatureThe solution was then cooled
  2. customevaporated to dryness under reduced pressure
  3. customthe residue obtained
  4. customthe solvent was removed
  5. customThe residue was chromatographed on silica gel (dichloromethane-methanol (98:2) as eluant)

Sources & evidence

ORD record
ord-ee9517859f504e7b8d3452e115c121ae
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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