Water → 1-(4-Chloro-butyl)-4-(6-methyl-pyridin-2-yl)-1H-pyrimidin-2-one

HRID 1514414Notes

Reaction equation

HRID 1514414 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:18][CH2:19][CH2:20][CH2:21][Cl:22].O>CN(C=O)C>[Cl:22][CH2:21][CH2:20][CH2:19][CH2:18][N:11]1[CH:12]=[CH:13][C:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=2)=[N:9][C:10]1=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutaneHCID 178424557HCID 178424557, compound

Product 1

HCID 592428011-(4-Chloro-butyl)-4-(6-methyl-pyridin-2-yl)-1H-pyrimidin-2-oneYield 58.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(6-methyl-pyridin-2-yl)-1H-pyrimidin-2-one (200 mg, 1.06 mmol) in dry DMF (20 ml), 60% NaH (55 mg, 1.39 mmol) was added portionwise. After heating the mixture at 100° C. for 1 hour, 1-bromo-4-chloro-butane (187 μl 1.39 mmol) was added and the mixture was stirred overnight at room temperature. 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. The residue was triturated with petroleum ether to give 173 mg of the title compound as a solid (58% 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
  6. customThe residue was triturated with petroleum ether

Sources & evidence

ORD record
ord-00146b9c16d642a6af3699a9e5b12a7d
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

Loading…