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

HRID 2091929Notes

Reaction equation

HRID 2091929 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) is stirred at room temperature for 24 h. The resulting precipitate is 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 is collected by vacuum filtration
  2. washwashed with small amounts of MeOH and water

Sources & evidence

ORD record
ord-f7e26e2eb49a4699a7efb809cb220cab
Source dataset
uspto-grants-2013_05
Patent number
US08440681B2

Reaction notes

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