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

HRID 1351144
Notes
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Reaction equation

HRID 1351144 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 702
Ethanol
Solvent

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-ef8128411227497ca32410a504f325f2
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07217715B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes