Methanol → HCID 11487560, compound

HRID 908509Notes

Reaction equation

HRID 908509 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:13]=[CH:12][C:10](=[O:11])[NH:9][C:7]1=[O:8].[C:14]1([Si:20](Cl)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CO>N1C=CC=CC=1>[C:27]1([Si:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[CH:13]=[CH:12][C:10](=[O:11])[NH:9][C:7]2=[O:8])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 64581,1',1''-(Chlorosilylidyne)tris(benzene)HCID 123533871-(4-Hydroxybutyl)pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 11487560HCID 11487560, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

1-(4′-Hydroxybutyl)uracil (0.048 g, 0.26 mmol) was dissolved in dry pyridine (1.5 mL) and cooled in an ice-salt bath. A solution of triphenylsilyl chloride (0.099 g, 0.34 mmol) in dry pyridine (1.5 mL) was added drop-wise. The reaction mixture was kept at 0° C. under nitrogen for 2 h 30. CH3OH (15 μL) was added and after 10 min the solution was concentrated on the rotary evaporator. The resultant crude transparent oil was purified by silica gel chromatography using a gradient elution of 0→3% CH3OH in CHCl3. The title compound was obtained as a white solid (0.085 g, 74%) from the fractions with Rf=0.50 (10% CH3OH/CHCl3).

Workup

  1. temperaturecooled in an ice-salt bath
  2. concentrationwas concentrated on the rotary evaporator
  3. customThe resultant crude transparent oil was purified by silica gel chromatography
  4. washa gradient elution of 0→3% CH3OH in CHCl3

Sources & evidence

ORD record
ord-99866b8cc35a4273bb83c6f51130f730
Source dataset
uspto-grants-2011_09
Patent number
US08017620B2

Reaction notes

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