(2E)-3-(dimethylamino)-1-[4-(trifluoromethyl)phenyl]prop-2-en-1-one → N-phenyl-4-[4-(trifluoromethyl)phenyl]pyrimidin-2-amine

HRID 1715690Notes

Reaction equation

HRID 1715690 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)=O.[CH:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]([NH2:27])[NH2:26])=[CH:20][CH:19]=1.C(O)(O)=O>CN1C(=O)CCC1.O>[C:21]1([NH:24][C:25]2[N:27]=[C:5]([C:7]3[CH:12]=[CH:11][C:10]([C:13]([F:14])([F:15])[F:16])=[CH:9][CH:8]=3)[CH:4]=[CH:3][N:26]=2)[CH:22]=[CH:23][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 5714026(2E)-3-(dimethylamino)-1-[4-(trifluoromethyl)phenyl]prop-2-en-1-oneHCID 16217093Carbonic acid, compound with phenylguanidine (1:1)

Product 1

HCID 57446828N-phenyl-4-[4-(trifluoromethyl)phenyl]pyrimidin-2-amineYield 88.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of (2E)-3-(dimethylamino)-1-[4-(trifluoromethyl)phenyl]prop-2-en-1-one (0.49 g, 2 mmol) and phenylguanidine carbonate salt (0.30 g, 2.2 mmol) in NMP (4 ml), is stirred at 120° C. for 2 days. It is then cooled to room temperature and diluted with water (40 ml). The resulting suspension is filtered, and the precipitate is washed with 50% ammonium chloride solution, water, and hexanes, and then dried in vacuo to give 0.56 g of an off-white solid; mp 162-163° C.; HRMS: calcd for C17H12F3N3, 315.0983; found (ESI_FTMS, [M+H]1+), 316.1048.

Workup

  1. filtrationThe resulting suspension is filtered
  2. washthe precipitate is washed with 50% ammonium chloride solution, water, and hexanes
  3. customdried in vacuo

Sources & evidence

ORD record
ord-ced25d957d7849bbab3f8b18092cb47f
Source dataset
uspto-grants-2010_09
Patent number
US07799915B2

Reaction notes

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