Chloroacetyl chloride → HCID 67028039, compound

HRID 2192394Notes

Reaction equation

HRID 2192394 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[Cl:9][CH2:10][C:11](Cl)=[O:12]>ClCCCl>[Cl:9][CH2:10][C:11]([NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[N:7]=1)=[O:12]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 2957632-Methylpyrimidin-4-amine

Product 1

HCID 67028039HCID 67028039, compoundYield 7.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

2-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 to give a solid that was filtered, 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 (70 mg, 7.5%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customto give a solid
  3. filtrationthat was filtered
  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-0ff78507101f4f73b37b2d18b142515d
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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