1,1',1''-(Chlorosilylidyne)tris(benzene) → HCID 11655779, compound

HRID 908520Notes

Reaction equation

HRID 908520 reaction equation
[C:1]1([Si:7](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[CH:35]=[CH:34][C:32](=[O:33])[NH:31][C:29]1=[O:30]>N1C=CC=CC=1>[C:1]1([Si:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]2[CH:35]=[CH:34][C:32](=[O:33])[NH:31][C:29]2=[O:30])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 64581,1',1''-(Chlorosilylidyne)tris(benzene)2×HCID 44413566HCID 44413566, compound

Product 1

HCID 11655779HCID 11655779, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent3×

Procedure

A solution of triphenylsilyl chloride (0.337 g, 1.14 mmol) in dry pyridine (3 mL) was added drop-wise to a solution of 1-(6′-hydroxyhexyl)uracil (0.200 g, 0.94 mmol) in dry pyridine (4 mL) cooled in an ice-salt bath. The reaction mixture was kept at 0° C. under nitrogen for 3 h30. As TLC monitoring evidenced the presence of unreacted starting material, triphenylsilyl chloride (0.325 g, 1.10 mmol) in dry pyridine (1 mL) was added. After a further 45 min at 0° C., the reaction had reached completion and was quenched with CH3OH (0.1 mL). 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 with a gradient elution of 0→5% CH3OH in CHCl3. The title compound was obtained as a white solid (0.140 g, 32%) from the fractions with Rf=0.52 (10% CH3OH/CHCl3). Some starting material (0.130 g, 65%) was also recovered, possibly resulting from hydrolysis during the work up.

Workup

  1. temperaturecooled in an ice-salt bath
  2. customwas kept at 0° C. under nitrogen for 3 h30
  3. additionwas added
  4. customwas quenched with CH3OH (0.1 mL)
  5. customRemoval of the solvent in vacuo
  6. customafforded a crude yellow oil which
  7. customwas purified by silica gel chromatography
  8. washwith a gradient elution of 0→5% CH3OH in CHCl3

Sources & evidence

ORD record
ord-95bd0eb668744b18adbe9c4ff7a9ffd9
Source dataset
uspto-grants-2011_09
Patent number
US08017620B2

Reaction notes

Loading…