Sodium Bisulfate → 2-(2-trifluoromethyl-phenyl)-3H-pyrido[2,3-d]pyrimidin-4-one

HRID 133142Notes

Reaction equation

HRID 133142 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=1[C:5]([NH:7][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([NH2:12])=[O:11])=O.[O-]CC.[K+].S([O-])(O)(=O)=O.[Na+]>C(O)C.O>[F:1][C:2]([F:22])([F:21])[C:3]1[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=1[C:5]1[NH:12][C:10](=[O:11])[C:9]2[CH:13]=[CH:14][CH:15]=[N:16][C:8]=2[N:7]=1

Participants

6

Reactant 3

HCID 516919Sodium BisulfateHCID 219392142-[2-(Trifluoromethyl)benzamido]pyridine-3-carboxamideHCID 23670592Potassium ethoxide

Product 1

HCID 1358508342-(2-trifluoromethyl-phenyl)-3H-pyrido[2,3-d]pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-(2-Trifluoromethyl-benzoylamino)-nicotinamide (800 mg, 2.6 mmol) is dissolved in 10 ml of ethanol. Potassium ethoxide (435 mg, 5.2 mmol) is added to the solution which is heated to reflux for 16 h. The reaction mixture is evaporated in vacuo to afford a gummy residue that is dissolved in water and acidified with 10% sodium hydrogen sulfate to pH 7. The resulting precipitate is filtered and dried under vacuum at 50 C to give 2-(2-trifluoromethyl-phenyl)-3H-pyrido[2,3-d]pyrimidin-4-one.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 16 h
  3. customThe reaction mixture is evaporated in vacuo
  4. customto afford a gummy residue that
  5. filtrationThe resulting precipitate is filtered
  6. customdried under vacuum at 50 C

Sources & evidence

ORD record
ord-11f992c72808480ba9d02f019eecc212
Source dataset
uspto-grants-2008_06
Patent number
US07390815B2

Reaction notes

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