Water → HCID 59242797, compound

HRID 1514430Notes

Reaction equation

HRID 1514430 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][NH:10][C:9](=[O:13])[N:8]=2)=[C:5]([CH3:14])[O:4][N: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:10]1[CH:11]=[CH:12][C:7]([C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=2[CH3:14])=[N:8][C:9]1=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutaneHCID 178434747HCID 178434747, compound

Product 1

HCID 59242797HCID 59242797, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(3,5-dimethyl-isoxazol-4-yl)-1H-pyrimidin-2-one (156 mg, 0.82 mmol) in dry DMF (20 ml), 60% NaH (40 mg, 1.06 mmol) was added portionwise under inert atmosphere. After heating the mixture at 100° C. for 1 hour, 1-bromo-4-chloro-butane (123 μl, 1.06 mmol) was added at room temperature and the mixture was heated at 100° 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 phase was dried (Na2SO4) and evaporated to afford 81 mg of the title compound that was used in the next step without further purification (35% yield).

Workup

  1. temperaturethe mixture was heated at 100° C. for 2 hours
  2. extractionthe mixture extracted with diethyl ether
  3. customto remove the dialkylated product
  4. dry with materialEthyl acetate phase was dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-a3f703e548934c18afda655258ccaac0
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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