Ammonia → HCID 19795171, compound

HRID 6246Notes

Reaction equation

HRID 6246 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([O:23][CH2:24][P:25]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26])[CH2:11][O:12][N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][CH:16]=[N:17][C:18]=2Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:33]>>[CH2:1]([O:8][CH2:9][CH:10]([O:23][CH2:24][P:25]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26])[CH2:11][O:12][N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][CH:16]=[N:17][C:18]=2[NH2:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 197951779-[3-Benzyloxy-2-(diethoxyphosphorylmethoxy)propoxy]-6-chloropurine

Product 1

HCID 19795171HCID 19795171, compoundYield 64%

Procedure

A solution of 9-[3-benzyloxy-2-(diethoxyphosphorylmethoxy)propoxy]-6-chloropurine (570 mg, 1.18 mmol) in ethanolic ammonia (10 ml) was heated in a sealed vessel at 110° C. for 2 hours. After cooling to ambient temperature, the solvent was evaporated and the residue obtained chromatographed on silica (dichloromethane/methanol 95:5 as eluant) to give the title compound (350 mg, 64%). IR: νmax (film) 3320, 3200, 2980, 2900, 640, 1595, 1470, 1450, 1410, 1390, 1370, 1330, 1290, 1240, 1160, 1090, 1050, 1020, 970, 820, 790, 730, 700, cm-1. 1H NMR: δH [(CD3)2SO] 1.22 (6H, t, J=7 Hz, OCH2CH3)2), 3.6-3.75 (2H, m, CH2OCH2Ph), 3.95-4.2 (7H, m, (OCH2CH3)2 +CH2CHCH2 +OCH2P), 4.4-4.65 (2H, m, N-OCH2), 4.52 (2H, s, OCH2Ph), 7.25-7.4 (5H, m, aromatic), 7.39 (2H, br.s, D2O exchangeable NH2), 8.15(1H, s), 8.41 (1H, s). Found: C, 49.81; H, 5.75; N, 14.07%; C20H28N5O6P. H2O requires: C, 49.68; H, 6.25; N, 14.48%, m/z: C20H28N5O5P requires 465.1777; observed: 467.1757.

Workup

  1. customthe solvent was evaporated
  2. customthe residue obtained
  3. customchromatographed on silica (dichloromethane/methanol 95:5 as eluant)

Sources & evidence

ORD record
ord-79f3846e5c26492db5b28dd5230190e2
Source dataset
uspto-grants-1993_09
Patent number
US05247085

Reaction notes

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