Benzenamine, 4-chloro-2-methoxy- → 4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-9-carboxylic acid N-(4-chloro-2-methoxy-phenyl)-amide

HRID 1914621Notes

Reaction equation

HRID 1914621 reaction equation
CO[C:3]([C:5]1[CH2:6][CH2:7][CH2:8][N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][N:17]=3)[NH:11][C:10]=12)=[O:4].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[C:25]([O:30][CH3:31])[CH:24]=1>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:3]([CH:5]2[C:10]3=[N:11][C:12]([C:16]4[CH:21]=[CH:20][N:19]=[CH:18][N:17]=4)=[CH:13][C:14](=[O:15])[N:9]3[CH2:8][CH2:7][CH2:6]2)=[O:4])=[C:25]([O:30][CH3:31])[CH:24]=1

Participants

6

Reactant 2

HCID 7143Benzenamine, 4-chloro-2-methoxy-HCID 67177666HCID 67177666, compound

Product 1

HCID 445960614-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-9-carboxylic acid N-(4-chloro-2-methoxy-phenyl)-amideYield 32.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 0.150 g (0.52 mmol) of (+/−)-4-oxo-2-pyrimidin-4-yl-1,6,7,8-tetrahydro-4H-pyrido[1,2-a]pyrimidine-9-carboxylic acid methyl ester in a sealed tube in 10.00 mL of toluene was added 0.825 g (5.24 mmol) of 4-chloro-2-methoxy-phenylamine and the resulting mixture was stirred under reflux for 16 hours. The mixture was dissolved in water and ethyl acetate. The organic phases were washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography (dichloromethane/methanol/ammoniac in proportions of 100/0/0 to 98/2/02) to afford 0.069 g (32%) of a solid.

Workup

  1. temperatureunder reflux for 16 hours
  2. washThe organic phases were washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by flash chromatography (dichloromethane/methanol/ammoniac in proportions of 100/0/0 to 98/2/02)

Sources & evidence

ORD record
ord-02339a9ef3424e56b81f0af786fa7ad7
Source dataset
uspto-grants-2013_12
Patent number
US08614219B2

Reaction notes

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