Water → HCID 59242776, compound

HRID 1514418Notes

Reaction equation

HRID 1514418 reaction equation
[F:1][C:2]1([F:18])[O:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][NH:14][C:13](=[O:17])[N:12]=3)[C:4]=2[O:3]1.[H-].[Na+].Br[CH2:22][CH2:23][CH2:24][CH2:25][Cl:26].O>CN(C=O)C>[Cl:26][CH2:25][CH2:24][CH2:23][CH2:22][N:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:4]3[O:3][C:2]([F:1])([F:18])[O:6][C:5]=3[CH:7]=[CH:8][CH:9]=2)=[N:12][C:13]1=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutaneHCID 178517422HCID 178517422, compound

Product 1

HCID 59242776HCID 59242776, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(2,2-difluoro-benzo[1,3]dioxol-4-yl)-1H-pyrimidin-2-one (232 mg, 0.92 mmol) in dry DMF (18 ml), 60% NaH (47 mg, 1.19 mmol) was added portionwise under inert atmosphere. After heating the mixture at 100° C. for 1 hour, 1-bromo-4-chloro-butane (137 μl 1.19 mmol) was added and the mixture was stirred overnight at room temperature. Water was added and the mixture extracted with diethyl ether. The organic layer was dried (Na2SO4) and evaporated. The residue purified by flash chromatography with hexane-ethyl acetate (8-2) to give 123 mg of the title compound (39% yield).

Workup

  1. extractionthe mixture extracted with diethyl ether
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated
  4. customThe residue purified by flash chromatography with hexane-ethyl acetate (8-2)

Sources & evidence

ORD record
ord-dc716b4e947349e6b2d1151d828b40c8
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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