Water → HCID 59242803, compound

HRID 1514422Notes

Reaction equation

HRID 1514422 reaction equation
[CH3:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[N:9]=2)=[CH:6][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:7]2[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=2)=[N:9][C:10]1=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutaneHCID 178432682HCID 178432682, compound

Product 1

HCID 59242803HCID 59242803, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(2-methyl-pyridin-3-yl)-1H-pyrimidin-2-one (199 mg, 1.06 mmol) in dry DMF (20 ml), 60% NaH (55 mg, 1.38 mmol) was added portionwise under inert atmosphere. After heating the mixture at 100° C. for 1 hour, 1-bromo-4-chloro-butane (160 μl, 1.38 mmol) was added and the mixture was stirred at room temperature for 1 hour and heated at 70° 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 161 mg of the title compound that was used in the next step without further purification (54% yield).

Workup

  1. temperatureheated at 70° 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-eb7507b0da4e4e408b747341c8c4bf29
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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