Sodium hydride → 1-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-5-(3-methyl-thiophen-2-yl)-1H-pyrimidine-2,4-dione

HRID 12662

Reaction equation

[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[C:8](=[O:14])[NH:9][C:10](=[O:13])[NH:11][CH:12]=1.[H-].[Na+].Br[CH2:18][CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>CN(C=O)C>[C:25]([Si:22]([CH3:24])([CH3:23])[O:21][CH2:20][CH2:19][CH2:18][N:11]1[CH:12]=[C:7]([C:3]2[S:4][CH:5]=[CH:6][C:2]=2[CH3:1])[C:8](=[O:14])[NH:9][C:10]1=[O:13])([CH3:28])([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 5-(3-methyl-thiophen-2-yl)-1H-pyrimidine-2,4-dione (Prep26, 110 mg, 0.52 mmol) in dry DMF (10 mL), 60% NaH (31 mg, 0.78 mmol) was added. The mixture was then heated at 100° C. for 1 hour. (3-bromo-propoxy)-tert-butyl-dimethyl-silane (180 μl, 0.7 mmol) was then added at room temperature and the reaction was stirred overnight. The solvent was evaporated and the crude was partitioned between NaHCO3 and Et2O. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (2-8) to give the title compound as a white solid (73 mg, 37% yield).

Workup

additionwas added
customThe solvent was evaporated
customthe crude was partitioned between NaHCO3 and Et2O
dry with materialThe organic phase was dried (Na2SO4)
customevaporated
customThe crude was purified by flash chromatography with ethyl acetate-petroleum ether (2-8)

Sources & evidence

ORD record: ord-02bf8d507037412cb69175d867be4cb6
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07727988B2

Linked notes

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