1,1',1''-(Chlorosilylidyne)tris(benzene) → 1-(3-Triphenylsilyloxypropyl)uracil

HRID 1713368Notes

Reaction equation

HRID 1713368 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH:12]=[CH:11][C:9](=[O:10])[NH:8][C:6]1=[O:7].[C:13]1([Si:19](Cl)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1>[C:26]1([Si:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:1][CH2:2][CH2:3][CH2:4][N:5]2[CH:12]=[CH:11][C:9](=[O:10])[NH:8][C:6]2=[O:7])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 64581,1',1''-(Chlorosilylidyne)tris(benzene)2×HCID 116007431-(3-Hydroxypropyl)uracil

Product 1

HCID 116260951-(3-Triphenylsilyloxypropyl)uracil

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent3×

Procedure

1-(3′-hydroxypropyl)uracil (0.193 g, 1.134 mmol) was dissolved in dry pyridine (4 mL) and cooled in an ice-salt bath. A solution of triphenylsilyl chloride (0.432 g, 1.46 mmol) in dry pyridine (3 mL) was added drop-wise. The reaction mixture was kept at 0° C. under nitrogen for 4 h30. As TLC monitoring evidenced the presence of unreacted starting material, more triphenyl silyl chloride (0.204 g, 0.69 mmol) in dry pyridine (1 mL) was added. After a further 15 min at 0° C., the reaction had reached completion and was quenched with CH3OH (50 μL). Removal of the solvent in vacuo afforded a crude yellow oil which was purified by silica gel chromatography, using a Jones Chromatography Isolute SI column eluted with a gradient of 0→5% CH3OH in CHCl3. The title compound was obtained as a white solid (0.392 g, 81%) from the fractions with Rf=0.52 (10% CH3OH/CHCl3). Some compound starting material was also recovered (34 mg, 18%).

Workup

  1. temperaturecooled in an ice-salt bath
  2. customwas kept at 0° C. under nitrogen for 4 h30
  3. additionwas added
  4. customwas quenched with CH3OH (50 μL)
  5. customRemoval of the solvent in vacuo
  6. customafforded a crude yellow oil which
  7. customwas purified by silica gel chromatography
  8. washeluted with a gradient of 0→5% CH3OH in CHCl3

Sources & evidence

ORD record
ord-11d81734b3384ff9a37f43ae79300767
Source dataset
uspto-grants-2010_09
Patent number
US07795270B2

Reaction notes

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