2,4,5-Trichloropyrimidine → 3-(2,5-dichloropyrimidin-4-ylamino)pyridin-2(1H)-one

HRID 1897652Notes

Reaction equation

HRID 1897652 reaction equation
[NH2:1][C:2]1[C:3](=[O:8])[NH:4][CH:5]=[CH:6][CH:7]=1.[Cl:9][C:10]1[N:15]=[C:14](Cl)[C:13]([Cl:17])=[CH:12][N:11]=1.C([O-])(O)=O.[Na+]>CO.O>[Cl:9][C:10]1[N:15]=[C:14]([NH:1][C:2]2[C:3](=[O:8])[NH:4][CH:5]=[CH:6][CH:7]=2)[C:13]([Cl:17])=[CH:12][N:11]=1

Participants

6

Reactant 3

HCID 2372592,4,5-TrichloropyrimidineHCID 3223533-Amino-2-pyridinolHCID 516892Sodium Bicarbonate

Product 1

HCID 582551623-(2,5-dichloropyrimidin-4-ylamino)pyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3-aminopyridin-2(1H)-one (99 mg, 0.90 mmol), 2,4,5-trichloropyrimidine (165 mg, 0.90 mmol, 1 equiv.) and NaHCO3 (76 mg, 0.90 mmol, 1 equiv.) in a mixture of MeOH (6 mL) and H2O (3 mL) was stirred at room temperature for 24 h. The resulting precipitate was collected by vacuum filtration and washed with small amounts of MeOH and water, providing the product 3-(2,5-dichloropyrimidin-4-ylamino)pyridin-2(1H)-one; ESMS m/z 257.0 (M+H+).

Workup

  1. filtrationThe resulting precipitate was collected by vacuum filtration
  2. washwashed with small amounts of MeOH and water

Sources & evidence

ORD record
ord-108d7898e8d7406f8c435f2ef03c8ecd
Source dataset
uspto-grants-2013_08
Patent number
US08519129B2

Reaction notes

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