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

HRID 339747Notes

Reaction equation

HRID 339747 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.C(N(CC)CC)C.Cl[CH2:29][C:30]1[O:34][C:33]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:32][CH:31]=1>ClCCl>[CH3:20][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:1][CH2:29][C:30]2[O:34][C:33]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:32][CH:31]=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 8471TriethylamineHCID 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 6344DichloromethaneSolvent

Procedure

A mixture of 4-amino-6-methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}pyrimidine (2 g), triethylamine (0.76 g), ethyl 5-chloromethyl-2-furancarboxylate (1.4 g) and dichloromethane (60 ml) was heated to reflux while stirring for 72 hours. The mixture thus obtained was concentrated under reduced pressure. After the resultant residue was washed with water added thereto, an organic phase was dried over anhydrous sodium sulfate and then evaporated. The evaporation residue was purified by column chromatography to obtain a target substance (0.5 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. temperatureto reflux
  3. customThe mixture thus obtained
  4. concentrationwas concentrated under reduced pressure
  5. washAfter the resultant residue was washed with water
  6. additionadded
  7. dry with materialan organic phase was dried over anhydrous sodium sulfate
  8. customevaporated
  9. customThe evaporation residue was purified by column chromatography
  10. customto obtain a target substance (0.5 g)

Sources & evidence

ORD record
ord-f4a2d12236a442c6a1da9a1744a4532d
Source dataset
uspto-grants-2014_11
Patent number
US08895565B2

Reaction notes

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