Water → 1-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-4-(2-fluoro-phenyl)-1H-pyrimidin-2-one

HRID 1514433Notes

Reaction equation

HRID 1514433 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][NH:11][C:10](=[O:14])[N:9]=1.[H-].[Na+].[C:17]([Si:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28]I)([CH3:23])[CH3:22])([CH3:20])([CH3:19])[CH3:18].O>CN(C=O)C>[C:17]([Si:21]([CH3:22])([CH3:23])[O:24][CH2:25][CH2:26][CH2:27][CH2:28][N:11]1[CH:12]=[CH:13][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[N:9][C:10]1=[O:14])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 4250746tert-Butyl(4-iodobutoxy)dimethylsilaneHCID 178517452HCID 178517452, compound

Product 1

HCID 592427901-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-4-(2-fluoro-phenyl)-1H-pyrimidin-2-oneYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(2-fluoro-phenyl)-1H-pyrimidin-2-one (375 mg, 1.97 mmol) in dry DMF (50 ml), 60% NaH (103 mg, 2.56 mmol) was added portionwise. After heating the mixture at 100° C. for 1 hour, tert-butyl-(4-iodo-butoxy)-dimethyl-silane (664 μl 2.56 mmol) was added at room temperature and the mixture was stirred overnight. Water was added and the mixture extracted with diethyl ether; the organic layer was dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography with petroleum ether-ethyl acetate (1-1) to give 370 mg of the title compound as a yellow solid (50% yield).

Workup

  1. extractionthe mixture extracted with diethyl ether
  2. dry with materialthe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash chromatography with petroleum ether-ethyl acetate (1-1)

Sources & evidence

ORD record
ord-86f2515faeac4349840034c5d01b6670
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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