Water → 1-(4-Chloro-butyl)-4-(2,4-dimethyl-thiazol-5-yl)-1H-pyrimidin-2-one

HRID 1514443Notes

Reaction equation

HRID 1514443 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[N:9]=2)=[C:5]([CH3:7])[N:6]=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:4]2[S:3][C:2]([CH3:1])=[N:6][C:5]=2[CH3:7])=[N:9][C:10]1=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutaneHCID 178432715HCID 178432715, compound

Product 1

HCID 592427831-(4-Chloro-butyl)-4-(2,4-dimethyl-thiazol-5-yl)-1H-pyrimidin-2-oneYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(2,4-Dimethyl-thiazol-5-yl)-1H-pyrimidin-2-one (120 mg, 0.58 mmol) in dry DMF (21 ml), 60% NaH (24 mg, 0.75 mmol) was added portionwise under inert atmosphere. After heating the mixture at 100° C. for 1 hour, 1-bromo-4-chloro-butane (86 μl, 0.75 mmol) was added at room temperature and the mixture was stirred overnight then was heated at 69° C. for 2 hours. 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 80 mg of the title compound as a solid (48% yield).

Workup

  1. temperaturethen was heated at 69° C. for 2 hours
  2. extractionthe mixture extracted with diethyl ether
  3. customto remove the dialkylated product
  4. washEthyl acetate was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-3a0559ca8f934a39bae6c5928de1038e
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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