4-amino-N,N-diethylbenzamide → 2-[[4-(Diethylaminocarbonyl)phenyl]amino]-4-(methylamino)-5-nitropyrimidine

HRID 1375392Notes

Reaction equation

HRID 1375392 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=1.[NH2:13][C:14]1[CH:26]=[CH:25][C:17]([C:18]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=1>C1COCC1.CC(O)C.O>[CH2:23]([N:20]([CH2:21][CH3:22])[C:18]([C:17]1[CH:25]=[CH:26][C:14]([NH:13][C:2]2[N:7]=[C:6]([NH:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=2)=[CH:15][CH:16]=1)=[O:19])[CH3:24]

Participants

6

Reactant 2

HCID 4587604-amino-N,N-diethylbenzamideHCID 71472322-chloro-N-methyl-5-nitropyrimidin-4-amine

Product 1

HCID 587867992-[[4-(Diethylaminocarbonyl)phenyl]amino]-4-(methylamino)-5-nitropyrimidineYield 87.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of 0.943 g (5 mmol) of 2-chloro-4-(methylamino)-5-nitropyrimidine in 25 mL THF is added a solution of 2.11 g (11 mmol) of 4-amino-N,N-diethylbenzamide in 100 mL of 2-propanol, and the resulting mixture is heated and stirred at reflux for 1 hour. The mixture is then diluted with water, the solid precipitate is collected, washed with water, and dried, to give 1.50 g (87%) of the title compound: mp (EtOH) 213–215° C.

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureat reflux for 1 hour
  3. customthe solid precipitate is collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-c9039a34d1da40bf898198070f6cf522
Source dataset
uspto-grants-2007_01
Patent number
US07169778B2

Reaction notes

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