Methyl iodide → (+/-)-9-Methyl-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 1914622Notes

Reaction equation

HRID 1914622 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[C:16]3=[N:17][C:18]([C:22]4[CH:27]=[CH:26][N:25]=[CH:24][N:23]=4)=[CH:19][C:20](=[O:21])[N:15]3[CH2:14][CH2:13][CH2:12]2)=[O:10])=[C:4]([O:28][CH3:29])[CH:3]=1.[H-].[Na+].[CH3:32]I>CN(C)C=O.O.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2([CH3:32])[C:16]3=[N:17][C:18]([C:22]4[CH:27]=[CH:26][N:25]=[CH:24][N:23]=4)=[CH:19][C:20](=[O:21])[N:15]3[CH2:14][CH2:13][CH2:12]2)=[O:10])=[C:4]([O:28][CH3:29])[CH:3]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 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)-amide

Product 1

HCID 44596062(+/-)-9-Methyl-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)-amideYield 51.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 0.100 g (0.24 mmol) of 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 (example 1) in 1.00 mL of dimethylformamide was added 0.010 g (0.24 mmol) of sodium hydride at 0° C. and the resulting mixture was stirred at room temperature for 2 hours. 0.020 mL (0.24 mmol) of methyl iodide was added and the mixture was stirred at room temperature for 1 hour. The mixture was dissolved in water and dichloromethane. 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 (cyclohexane/ethyl acetate in proportions of 80/20 to 70/30) to afford 0.053 g (51%) of a solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  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 (cyclohexane/ethyl acetate in proportions of 80/20 to 70/30)

Sources & evidence

ORD record
ord-f318ad9e9ee74a5ab7dbc5dda03356ee
Source dataset
uspto-grants-2013_12
Patent number
US08614219B2

Reaction notes

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