Water → 1-(4-Chloro-butyl)-4-pyridin-3-yl-1H-pyrimidin-2-one

HRID 1514439Notes

Reaction equation

HRID 1514439 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][NH:10][C:9](=[O:13])[N:8]=2)[CH:2]=1.[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][CH2:20][Cl:21].O>CN(C=O)C>[Cl:21][CH2:20][CH2:19][CH2:18][CH2:17][N:10]1[CH:11]=[CH:12][C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[N:8][C:9]1=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutaneHCID 178517515HCID 178517515, compound

Product 1

HCID 592427981-(4-Chloro-butyl)-4-pyridin-3-yl-1H-pyrimidin-2-oneYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-pyridin-3-yl-1H-pyrimidin-2-one (50 mg, 0.29 mmol) in dry DMF (11 ml), 60% NaH (15 mg, 0.37 mmol) was added portionwise under inert atmosphere. After heating the mixture at 100° C. for 1 hour, 1-bromo-4-chloro-butane (43 μl, 0.37 mmol) was added at room temperature and the mixture was stirred overnight. Water was added and the mixture extracted with diethyl ether to remove the dialkylated product and finally with ethyl acetate. Ethyl acetate was washed with brine, dried (Na2SO4) and evaporated to give 40 mg of the title compound as a solid (54% yield).

Workup

  1. extractionthe mixture extracted with diethyl ether
  2. customto remove the dialkylated product
  3. washEthyl acetate was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-eca353f8691d4b0386d952fae4abfbe8
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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