Chloroacetyl chloride → 2-Chloro-N-(6-methyl-pyrimidin-4-yl)-acetamide

HRID 2192396Notes

Reaction equation

HRID 2192396 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[Cl:9][CH2:10][C:11](Cl)=[O:12]>ClCCCl>[Cl:9][CH2:10][C:11]([NH:8][C:4]1[CH:3]=[C:2]([CH3:1])[N:7]=[CH:6][N:5]=1)=[O:12]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 5728526-Methylpyrimidin-4-amine

Product 1

HCID 673110012-Chloro-N-(6-methyl-pyrimidin-4-yl)-acetamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

6-Methyl-pyrimidin-4-yl amine (545 mg) was suspended in DCE (5 mL) and chloroacetylchloride (0.4 mL) was added dropwise. The reaction was heated in a microwave at 80° C. for 5 mins. The reaction mixture was cooled, filtered and a solid obtained. The reaction was repeated a second time and both batches of solid were combined, washed with dichloromethane then suspended in dichloromethane and sat. NaHCO3 (aq.) was added. The organic phase was collected and the aqueous layer extracted with dichloromethane (×2). The combined organic layer was dried over sodium sulphate and concentrated. The crude product was purified by silica gel chromatography eluting with 0-10% MeOH/dichloromethane to give the sub-titled compound as a yellow solid (120 mg).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. customa solid obtained
  4. washwashed with dichloromethane
  5. additionsat. NaHCO3 (aq.) was added
  6. customThe organic phase was collected
  7. extractionthe aqueous layer extracted with dichloromethane (×2)
  8. dry with materialThe combined organic layer was dried over sodium sulphate
  9. concentrationconcentrated
  10. customThe crude product was purified by silica gel chromatography
  11. washeluting with 0-10% MeOH/dichloromethane

Sources & evidence

ORD record
ord-1eb3fa1fdb7f40f680bbcd6ed7731817
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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