Water → HCID 67997597, compound

HRID 1425984Notes

Reaction equation

HRID 1425984 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH:9]1[CH2:13][CH2:12][CH2:11][C:10]1=[O:14].C([O-])([O-])=O.[K+].[K+].O>CN1CCCC1=O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 120252-PyrrolidoneHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 67997597HCID 67997597, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-2-chloropyrimidine (11.3 g), pyrrolidin-2-one (5 g), and K2CO3 (27.4 g) in 1-methylpyrrolidin-2-one (100 mL) was heated to 80° C. under nitrogen and stirred at this temperature overnight. After cooling to room temperature, the reaction mixture was concentrated to give an oil which was poured into water (50 mL). The resulting mixture was extracted with ethyl acetate (3×50 mL) and the combined organic phase was concentrated to afford an oil, which was purified by column chromatography on silica gel to afford the title compound. Yield: 592 mg (4% of theory).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated
  3. customto give an oil which
  4. extractionThe resulting mixture was extracted with ethyl acetate (3×50 mL)
  5. concentrationthe combined organic phase was concentrated
  6. customto afford an oil, which
  7. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e6ed56458c1d4725b28eef28d7ebd97e
Source dataset
uspto-grants-2015_01
Patent number
US08933072B2

Reaction notes

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