Dihydrouracil → 3-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-dihydropyrimidine-2,4(1H,3H)-dione

HRID 1245344Notes

Reaction equation

HRID 1245344 reaction equation
[NH:1]1[CH2:8][CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[Si:9]([O:16][CH2:17][CH2:18][CH2:19]O)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Si:9]([O:16][CH2:17][CH2:18][CH2:19][N:4]1[C:5](=[O:6])[CH2:7][CH2:8][NH:1][C:2]1=[O:3])([C:12]([CH3:13])([CH3:14])[CH3:15])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 649DihydrouracilHCID 10796Cesium carbonateHCID 40777913-[(Tert-butyldimethylsilyl)oxy]propan-1-ol

Product 1

HCID 587195673-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-dihydropyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture 5,6-dihydrouracil (4.45 g, 39.028 mmol), 3-{[tert-butyl(dimethyl)silyl]oxy}propan-1-ol (3 mL, 13.01 mmol) and Cs2CO3 (16.95 g, 52.04 mmol) in dry DMF (120 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. Combined organic extracts were washed with water and brine, dried over Na2SO4 and the solvent evaporated in vacuo. Purified by chromatography on silica gel using ethyl acetate and hexane (60:40) to give the title compound.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washCombined organic extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. customthe solvent evaporated in vacuo
  5. customPurified by chromatography on silica gel

Sources & evidence

ORD record
ord-ab6d7a56bb0f42afacd71a53f3b34f8f
Source dataset
uspto-grants-2006_10
Patent number
US07125865B2

Reaction notes

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