Ammonia → HCID 19808654, compound

HRID 373902Notes

Reaction equation

HRID 373902 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][CH:16]([CH2:27][O:28]C(=O)C)[CH2:17][CH2:18][P:19]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:20].[NH3:32]>>[NH2:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][N:6]2[O:14][CH2:15][CH:16]([CH2:27][OH:28])[CH2:17][CH2:18][P:19]([O:21][CH2:22][CH3:23])([O:24][CH2:25][CH3:26])=[O:20])=[C:2]([NH2:32])[N:10]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 19808616HCID 19808616, compound

Product 1

HCID 19808654HCID 19808654, compoundYield 45%

Procedure

6-Chloro 9-[2-(acetoxymethyl)-4-(diethoxyphosphoryl)-butoxy]-2-formamidopurine (0.110 g, 0.23 mmol) was dissolved in ethanolic ammonia solution (5 ml) and the resulting reaction mixture was kept at 110°0 C. for 6 hours. The solution was allowed to cool, the solvent was evaporated and the residue chromatographed on silica gel (eluting with chloroform 9:1) to yield the title compound (40 mg, 45%). 1H NMR: δH [(CD3)2SO] 1.22 (6H, t, (OCH2CH3)2), 1.76 (5H, m, CHCH2CH2P), 3.49 (2H, br.s, CH2OH), 3.99 (4H, m, (OCH2CH3)2), 4.25 (2H, m, NOCH2), 4.72 (1H, br.s, D2O exchangeable CH2OH), 5.9 (2H, br.s, D2O exchangeable, NH2), 6.79 (2H, br.s, D2O exchangable, NH2), 8.31 (1H, s, H-8).

Workup

  1. customthe resulting reaction mixture
  2. temperatureto cool
  3. customthe solvent was evaporated
  4. customthe residue chromatographed on silica gel (eluting with chloroform 9:1)

Sources & evidence

ORD record
ord-e7277fb5844f4e0a98140e5f58d40869
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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