Water → HCID 9823773, compound

HRID 1167628Notes

Reaction equation

HRID 1167628 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[N:3]=1.[NH2:24][CH2:25][C:26]([N:28]([CH:30]1[CH2:32][CH2:31]1)[CH3:29])=[O:27].C(N(CC)CC)C.O>C(Cl)(Cl)Cl>[CH:30]1([N:28]([CH3:29])[C:26](=[O:27])[CH2:25][NH:24][C:2]2[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:5]=[C:4]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[N:3]=2)[CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12093257HCID 12093257, compoundHCID 12093258HCID 12093258, compound

Product 1

HCID 9823773HCID 9823773, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-chloro-6-phenyl-2-(4-trifluoromethylphenyl)-pyrimidine (15 g), 2-amino-N-cyclopropyl-N-methylacetamide (10 g) and triethylamine (5.4 g) is heated at 150° C. under reflux for 2 hours. To the reaction mixture are added water and chloroform, and the chloroform layer is separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: chloroform), and recrystallized from ethanol to give the desired compound (17 g).

Workup

  1. temperatureunder reflux for 2 hours
  2. customthe chloroform layer is separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel column chromatography (eluent: chloroform)
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d813afdf16464cd98bb5579e47c813e4
Source dataset
uspto-grants-2003_09
Patent number
US06620817B1

Reaction notes

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