Water → 1-(4-Chloro-butyl)-5-methyl-4-pyridin-3-yl-1H-pyrimidin-2-one

HRID 1514410Notes

Reaction equation

HRID 1514410 reaction equation
[CH3:1][C:2]1[C:3]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.[H-].[Na+].Br[CH2:18][CH2:19][CH2:20][CH2:21][Cl:22].O>CS(C)=O>[Cl:22][CH2:21][CH2:20][CH2:19][CH2:18][N:6]1[CH:7]=[C:2]([CH3:1])[C:3]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[N:4][C:5]1=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutaneHCID 178430894HCID 178430894, compound

Product 1

HCID 592427851-(4-Chloro-butyl)-5-methyl-4-pyridin-3-yl-1H-pyrimidin-2-oneYield 68%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 5-methyl-4-pyridin-3-yl-1H-pyrimidin-2-one (100 mg, 0.53 mmol) in DMSO (2 ml), 60% NaH (23 mg, 0.59 mmol) was added portionwise. After heating the mixture at 60° C. for 1 hour, 1-bromo-4-chloro-butane (100 mg, 0.59 mmol) dissolved in DMSO (0.8 ml) was added at 60° C. and the heating was maintained for further 2 hours. After cooling to 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 to afford 100 mg of the title compound as yellow oil (68% yield).

Workup

  1. additionwas added at 60° C.
  2. temperaturethe heating was maintained for further 2 hours
  3. temperatureAfter cooling to room temperature
  4. extractionthe mixture extracted with diethyl ether
  5. customto remove the dialkylated product
  6. washEthyl acetate was washed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-58f559364c1d420cb123878f1c915fee
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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