2,6-Dimethoxypyridin-3-amine → (+/-)-4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydro-pyrimido[1,2-a]azepine-10-carboxylic acid N-(2,6-dimethoxy-pyridin-3-yl)-amide

HRID 1914628Notes

Reaction equation

HRID 1914628 reaction equation
[N+](C1C=CC(O[C:11]([CH:13]2[CH2:19][CH2:18][CH2:17][CH2:16][N:15]3[C:20](=[O:30])[CH:21]=[C:22]([C:24]4[CH:29]=[CH:28][N:27]=[CH:26][N:25]=4)[N:23]=[C:14]23)=[O:12])=CC=1)([O-])=O.[CH3:31][O:32][C:33]1[C:38]([NH2:39])=[CH:37][CH:36]=[C:35]([O:40][CH3:41])[N:34]=1>C(#N)C.CN(C)C1C=CN=CC=1.O.ClCCl>[CH3:31][O:32][C:33]1[C:38]([NH:39][C:11]([CH:13]2[CH2:19][CH2:18][CH2:17][CH2:16][N:15]3[C:20](=[O:30])[CH:21]=[C:22]([C:24]4[CH:29]=[CH:28][N:27]=[CH:26][N:25]=4)[N:23]=[C:14]23)=[O:12])=[CH:37][CH:36]=[C:35]([O:40][CH3:41])[N:34]=1

Participants

7

Reactant 2

HCID 5930052,6-Dimethoxypyridin-3-amineHCID 67178000(+/-)-4-Oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydro-pyrimido[1,2-a]azepine-10-carboxylic acid (4-nitro-phenyl) ester

Product 1

HCID 44594502(+/-)-4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydro-pyrimido[1,2-a]azepine-10-carboxylic acid N-(2,6-dimethoxy-pyridin-3-yl)-amideYield 26%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.450 g (1.10 mmol) of (+/−)-4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydro-pyrimido[1,2-a]azepine-10-carboxylic acid 4-nitro-phenyl ester in 10 mL of dry acetonitrile in a sealed tube, were added 0.341 g (2.21 mmol) of 2,6-dimethoxy-pyridin-3-ylamine and 0.270 g (2.21 mmol) of dimethyl-pyridin-4-yl-amine. The resulting mixture was stirred under reflux for 16 hours. 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 (dichloromethane/methanol/ammoniac in proportions of 100/0/0 to 98/2/02) to afford 0.121 g (26%) of a white 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-86b5e406be9f4f23a39e3938edc16bec
Source dataset
uspto-grants-2013_12
Patent number
US08614219B2

Reaction notes

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