Water → N-(5-Nitro-pyrimidin-2-yl)-benzamide

HRID 1767721Notes

Reaction equation

HRID 1767721 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[N:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=1.O>N1C=CC=CC=1>[C:1]([NH:10][C:11]1[N:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 764905-Nitropyrimidin-2-amine

Product 1

HCID 57699955N-(5-Nitro-pyrimidin-2-yl)-benzamideYield 47.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzoyl chloride (0.92 ml, 7.93 mmol) was added dropwise to a stirred solution of 2-amino-5-nitropyrimidine (1.00 g, 7.14 mmol) in pyridine (20 ml) and the reaction was heated at reflux for 4 hours under an inert atmosphere. The reaction was allowed to cool to ambient temperature, poured into water (200 ml) and allowed to stand for 16 hours. The solid was collected by suction filtration, washed with water (3×20 ml) and dried in vacuo. An oil residue on the surface of the aqueous phase was dissolved in dichloromethane (50 ml) and then purified by flash chromatography on silica gel, eluting with 1–3% methanol in dichloromethane. The two materials were identical and yielded 2-(N-benzoyl)amino-5-nitropyrimidine (826 mg, 47% yield) as a white solid:

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 4 hours under an inert atmosphere
  3. filtrationThe solid was collected by suction filtration
  4. washwashed with water (3×20 ml)
  5. customdried in vacuo
  6. dissolutionAn oil residue on the surface of the aqueous phase was dissolved in dichloromethane (50 ml)
  7. custompurified by flash chromatography on silica gel
  8. washeluting with 1–3% methanol in dichloromethane

Sources & evidence

ORD record
ord-7aa76a56b0774c7789627b85ea27c5ab
Source dataset
uspto-grants-2007_06
Patent number
US07235559B1

Reaction notes

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