Water → HCID 59242796, compound

HRID 1514426Notes

Reaction equation

HRID 1514426 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[N:9]=2)[CH:5]=[CH: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:11]1[CH:12]=[CH:13][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=2)=[N:9][C:10]1=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutaneHCID 178422843HCID 178422843, compound

Product 1

HCID 59242796HCID 59242796, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(2-methyl-pyridin-4-yl)-1H-pyrimidin-2-one (256 mg, 1.37 mmol) in dry DMF (45 ml), 60% NaH (71 mg, 1.78 mmol) was added portionwise under inert atmosphere. After heating the mixture at 100° C. for 1 hour, 1-bromo-4-chloro-butane (305 mg, 1.78 mmol) was added and the mixture was stirred at room temperature for 1.5 hours and heated at 60° C. for 2 hours. Water was added and the mixture extracted with diethyl ether and with ethyl acetate. The organic layers were mixed together, dried (Na2SO4) and evaporated to afford 100 mg of the title compound that was used in the next step without further purification in the next step (27% yield).

Workup

  1. temperatureheated at 60° C. for 2 hours
  2. extractionthe mixture extracted with diethyl ether and with ethyl acetate
  3. additionThe organic layers were mixed together
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-9c2a5ddb19264658931f4b7d7f11ebe0
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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