Potassium Carbonate → 4-Oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-1,4a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl ester

HRID 1520425Notes

Reaction equation

HRID 1520425 reaction equation
Cl.[CH2:2]([O:4][C:5]([N:7]1[CH2:13][CH2:12][C:11]([NH2:14])=[N:10][CH2:9][CH2:8]1)=[O:6])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[N:21]1[CH:26]=[CH:25][C:24]([C:27](=O)[CH2:28][C:29](OCC)=[O:30])=[N:23][CH:22]=1>C(O)C>[CH2:2]([O:4][C:5]([N:7]1[CH2:13][CH2:12][C:11]2=[N:14][C:27]([C:24]3[CH:25]=[CH:26][N:21]=[CH:22][N:23]=3)=[CH:28][C:29](=[O:30])[N:10]2[CH2:9][CH2:8]1)=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11961458Ethyl 3-oxo-3-(pyrimidin-4-yl)propanoateHCID 668416895-Amino-2,3,6,7-tetrahydro-[1,4]diazepine-1-carboxylic acid ethyl ester monohydrochloride

Product 1

HCID 668417894-Oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-1,4a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl esterYield 46.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 13.4 g (60.45 mmol) of 5-amino-2,3,6,7-tetrahydro-[1,4]diazepine-1-carboxylic acid ethyl ester monohydrochloride (synthesis as described in WO9716430) in 50 mL of ethanol was added 10.29 g (74.50 mmol) of potassium carbonate. The reaction mixture was stirred at room temperature for 10 min, 14.47 g (74.50 mmol) of ethyl 3-(4-pyrimidinyl)-3-oxopropionate was added and the resulting mixture was stirred under reflux for 2.5 hours. The cooled solution was evaporated to remove solvent. The mixture was dissolved with water and diethyl ether. After stirring, the resulting solid was filtered, washed with water and diethyl ether to afford 8.80 g (46%) of the desired compound as a powder.

Workup

  1. stirringthe resulting mixture was stirred
  2. temperatureunder reflux for 2.5 hours
  3. customThe cooled solution was evaporated
  4. customto remove solvent
  5. dissolutionThe mixture was dissolved with water and diethyl ether
  6. stirringAfter stirring
  7. filtrationthe resulting solid was filtered
  8. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-079b1368aedc46aaa89f37abc4b31d93
Source dataset
uspto-grants-2015_07
Patent number
US09073914B2

Reaction notes

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