Potassium Carbonate → 2-(4-Pyridinyl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one

HRID 746454Notes

Reaction equation

HRID 746454 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7](=O)[CH2:8][C:9]([O:11]CC)=O)=[CH:3][CH:2]=1.Cl.[F:16][C:17]([F:26])([F:25])[CH:18]1[NH:23][C:22]([NH2:24])=[N:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[N:24]=[C:22]3[NH:23][CH:18]([C:17]([F:26])([F:16])[F:25])[CH2:19][CH2:20][N:21]3[C:9](=[O:11])[CH:8]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionateHCID 230261764-(Trifluoromethyl)-1,4,5,6-tetrahydropyrimidin-2-amine hydrochloride

Product 1

HCID 1363464562-(4-Pyridinyl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-oneYield 55.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.62 g (29.09 mmol) of ethyl 3-(pyridin-4-yl)-3-oxopropionate, 7 g (29.09 mmol) of 6-(trifluoromethyl)-1,4,5,6-tetrahydro-2-pyrimidinamine hydrochloride (1:2) and 10.05 g (72.72 mmol) of potassium carbonate in 50 ml of ethanol was heated at reflux temperature for 12 h. The cooled solution was evaporated to remove solvent, the residue was treated with water and the precipitate was filtered to give 4.82 g of product as a yellow powder.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 12 h
  3. customThe cooled solution was evaporated
  4. customto remove solvent
  5. additionthe residue was treated with water
  6. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-f6940863ce4649aabacc1459b04f40eb
Source dataset
uspto-grants-2008_07
Patent number
US07393853B2

Reaction notes

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