Potassium Carbonate → Ethyl 5-(6-methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidin-4-ylaminomethyl)-2-furancarboxylate

HRID 339749Notes

Reaction equation

HRID 339749 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[C:6]([CH3:20])[N:5]=[CH:4][N:3]=1.Cl[CH2:22][C:23]1[O:27][C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:20][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:1][CH2:22][C:23]2[O:27][C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:25][CH:24]=2)[C:7]=1[C:8]#[C:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylateHCID 680024494-Amino-6-methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidine

Product 1

HCID 44815753Ethyl 5-(6-methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidin-4-ylaminomethyl)-2-furancarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-amino-6-methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidine (2.8 g), ethyl 5-chloromethyl-2-furancarboxylate (1.8 g), potassium carbonate (2.1 g) and N,N-dimethylformamide (120 ml) was heated while stirring at 70° C. for 15 hours. The mixture thus obtained was concentrated under reduced pressure. To the resultant residue, water was added. After extraction was performed with chloroform, an organic phase was dried over anhydrous sodium sulfate and then evaporated. The evaporated residue was purified by column chromatography to obtain a target substance (1 g). The target substance was subjected to e.g., proton nuclear magnetic resonance spectrometry (1H-NMR) and mass spectrometry (MS) and confirmed as the titled compound. Furthermore, MS measurement result is shown.

Workup

  1. temperaturewas heated
  2. customThe mixture thus obtained
  3. concentrationwas concentrated under reduced pressure
  4. additionTo the resultant residue, water was added
  5. extractionAfter extraction
  6. dry with materialan organic phase was dried over anhydrous sodium sulfate
  7. customevaporated
  8. customThe evaporated residue was purified by column chromatography
  9. customto obtain a target substance (1 g)

Sources & evidence

ORD record
ord-e228e53003564ed7bc00513b74849d0e
Source dataset
uspto-grants-2014_11
Patent number
US08895565B2

Reaction notes

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