Pyridine → HCID 68777825, compound

HRID 2263112Notes

Reaction equation

HRID 2263112 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[NH2:7].N1C=CC=CC=1.Cl[C:15]([O:17][CH2:18][C:19]([Cl:22])([Cl:21])[Cl:20])=[O:16]>CN(C)C(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[NH:7][C:15](=[O:16])[O:17][CH2:18][C:19]([Cl:22])([Cl:21])[Cl:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 79782-AminopyrimidineHCID 870632,2,2-Trichloroethyl chloroformate

Product 1

HCID 68777825HCID 68777825, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of pyrimidine-2-amine (2.00 g, 21.0 mmol) and pyridine (5.10 ml, 63.0 mmol) in N,N-dimethylacetamide (50 ml) was added 2,2,2-trichloroethyl chloroformate (4.34 ml, 31.5 mmol) with ice-cooling, and the mixture was stirred for 40 minutes with ice-cooling. The reaction mixture was poured into ice-water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of hexane and ethyl acetate and the desired product (2.57 g, 45.2%) as a solid was collected by filtration.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was recrystallized from a mixed solvent of hexane and ethyl acetate
  8. filtrationthe desired product (2.57 g, 45.2%) as a solid was collected by filtration

Sources & evidence

ORD record
ord-1799398746484fda9aa8f3d625fe26b9
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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