HCID 19808606, compound → HCID 19808645, compound

HRID 373890Notes

Reaction equation

HRID 373890 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([O:21][NH:22][C:23]1[N:28]=[CH:27][N:26]=[C:25]([Cl:29])[C:24]=1[NH:30][CH:31]=O)[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]>C(OC(OCC)OCC)(=O)C>[Si:1]([O:8][CH2:9][CH:10]([O:21][N:22]1[CH:31]=[N:30][C:24]2[C:23]1=[N:28][CH:27]=[N:26][C:25]=2[Cl:29])[CH2:11][CH2:12][P:13]([O:15][CH2:16][CH3:17])([O:18][CH2:19][CH3:20])=[O:14])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 19808606HCID 19808606, compound

Product 1

HCID 19808645HCID 19808645, compoundYield 56%

Reagents, catalysts & solvents 1

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

Procedure

A solution of 6-[[1-(t-butyldimethylsilyloxymethyl)-3-(diethoxyphosphoryl)propoxy]amino]-4-chloro-5-formamidopyrimidine (0.5 g) in diethoxymethyl acetate (5 ml) was heated at 110° C. for 2 hours. The solvent was evaporated under reduced pressure, the residue dissolved in methanol (5 ml) and 0.880 ammonia (0.1 ml) added. After 30 minutes at ambient temperature, the solvent was evaporated and the residue chromatographed on silica gel using dichloromethane-methanol (98:2) as eluant. This afforded the title compound (0.27 g, 56%) as a yellow oil. IR: υmax (film) 2940, 2870, 1595, 1565, 1440, 1390, 1340, 1250, 1220, 1060, 1030, 970, 930, 840, 790 cm-1. 1H NMR: δH (CDCl3) 0.0 (6H, s, SiMe2), 0.8 (9H, s, SiBut), 1.25 (6H, t, J=7Hz, (OCH2CH3)2), 1.8-2.4 (4H, m, CH2CH2P) 3.8 (2H, d, J=6Hz, CH2OSi), 4.1 (4H, m, (OCH2CH3)2), 4.6 (1H, m, CHON), 8.35 (1H, s), 8.75 (1H, s). Found: C, 45.97; H, 6.89; N, 10.80%. C19H34N4O5PSiCl requires: C, 46.28; H, 6.95; N, 11.36%.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue dissolved in methanol (5 ml)
  3. addition0.880 ammonia (0.1 ml) added
  4. customthe solvent was evaporated
  5. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-2993c6ef46304033a81a36fd03e4e1f6
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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