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

HRID 12665

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+].I[CH2:18][CH2:19][CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].O>CN(C=O)C>[C:26]([Si:23]([CH3:24])([CH3:25])[O:22][CH2:21][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])([CH3:29])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 5-(3-methyl-thiophen-2-yl)-1H-pyrimidine-2,4-dione (Prep 26, 250 mg, 1.2 mmol) in DMF (10 mL), 60% NaH (58 mg, 1.44 mmol) was added portionwise. The reaction was then heated to 70° C. and this temperature was maintained for 1.5 hour. After cooling to room temperature, (4-iodo-butoxy)-tert-butyl-dimethyl-silane (452 mg, 1.44 mmol) was then added dropwise and the reaction was stirred for 24 hours. Water (30 mL) was added and the product was extracted with Et2O. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (15-85) followed by DCM/MeOH (70:30) to give the title compound as a yellow oil (110 mg, 23% yield).

Workup

temperaturethis temperature was maintained for 1.5 hour
temperatureAfter cooling to room temperature
extractionthe product was extracted with Et2O
dry with materialThe organic phase was dried (Na2SO4)
customevaporated
customThe crude was purified by flash chromatography with ethyl acetate-petroleum ether (15-85)

Sources & evidence

ORD record: ord-f8276ed10f254d9d97d0a20aa58f09dd
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07727988B2

Linked notes

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