Ammonia → 9-[1-(t-Butyldimethylsilyloxymethyl)-3-(diethoxy-phosphoryl)propoxy]adenine

HRID 373891Notes

Reaction equation

HRID 373891 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([O:21][N:22]1[CH:30]=[N:29][C:28]2[C:23]1=[N:24][CH:25]=[N:26][C:27]=2Cl)[CH2:11][CH2:12][P:13]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH3:32]>C(O)C>[Si:1]([O:8][CH2:9][CH:10]([O:21][N:22]1[CH:30]=[N:29][C:28]2[C:23]1=[N:24][CH:25]=[N:26][C:27]=2[NH2:32])[CH2:11][CH2:12][P:13]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 19808645HCID 19808645, compound

Product 1

HCID 198086079-[1-(t-Butyldimethylsilyloxymethyl)-3-(diethoxy-phosphoryl)propoxy]adenineYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 9-[1-(t-butyldimethylsilyloxymethyl)-3-(diethoxyphosphoryl)propoxy]-6-chloropurine (0.30 g) in ethanol (10 ml) saturated with ammonia gas was heated in a sealed vessel at 100° C. for 2 hours. The reaction mixture was cooled to ambient temperature overnight, the ethanol evaporated under reduced pressure and the residue chromatographed on silica gel using dichloro-methane-methanol (98:2) as eluant. Starting material (0.06 g) was recovered and the eluant was changed to dichloromethane-methanol (95:5) to afford the title compound (0.10 g, 43%) as an oil. 1H NMR: δH ((CD3)2)2SO) 0.00, 0.61 (6H, 2 x s, SiMe2). 0.81 (9H, s, SiBut), 1.20 (6H, t, J=7Hz, (OCH2CH3)2), 1.7-2.2 (4H, m, --CH2CH2P), 3.82 (2H, d, J=4.1 H, CH2OSi), 4.0 (4H, m, (OCH2CH3)2), 4.44 (1H, m, OCHCH2), 7.35 (2H, s, D2O exchangeable, N2), 8.3 (1H, s), 8.27 (1H, s). Found: C, 47.82; H, 7.61; N, 14.41%. C19H36N5O5SiP requires: C, 48.16; H, 7.66; N, 14.79%. m/z: C19H36N5O5SiP requires: 473.2221. Observed: 473.2219.

Workup

  1. customthe ethanol evaporated under reduced pressure
  2. customthe residue chromatographed on silica gel
  3. customStarting material (0.06 g) was recovered

Sources & evidence

ORD record
ord-43bc19db2c68424aba7f99059d69f30f
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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