Benzenamine, 4-(4-morpholinyl)- → 4-(Methylamino)-2-[(4-morpholinophenyl)amino]-5-nitropyrimidine

HRID 1375390Notes

Reaction equation

HRID 1375390 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:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:16][CH:15]=1>C1COCC1.CC(O)C.O>[CH3:9][NH:8][C:6]1[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=[C:2]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:18][CH:19]=2)[N:7]=1

Participants

6

Reactant 2

HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 71472322-chloro-N-methyl-5-nitropyrimidin-4-amine

Product 1

HCID 210775724-(Methylamino)-2-[(4-morpholinophenyl)amino]-5-nitropyrimidineYield 98.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

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 1.96 g (11 mmol) of 4-(4-aminophenyl)morpholine in 100 mL of 2-propanol, and the resulting mixture is heated and stirred at 50° C. for 30 minutes. The mixture is then diluted with water, the solid precipitate is collected, washed with water, and dried, to give 1.62 g (98%) of the title compound: mp (EtOH) 240–241° C.

Workup

  1. temperaturethe resulting mixture is heated
  2. customthe solid precipitate is collected
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-f332a0c8d2b14233babc4f79904b6635
Source dataset
uspto-grants-2007_01
Patent number
US07169778B2

Reaction notes

Loading…