Water → HCID 67997597, compound

HRID 1528594Notes

Reaction equation

HRID 1528594 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-919ff72e21e84ba3ae0c17e03081e4db
Source dataset
uspto-grants-2015_07
Patent number
US09090605B2

Reaction notes

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