Potassium Carbonate → 4,5-Diphenyl-6-(4-pyridin-2-yl-piperazin-1-yl)-2-(trifluoromethyl)pyrimidine

HRID 251417Notes

Reaction equation

HRID 251417 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:5]=[C:4]([C:20]([F:23])([F:22])[F:21])[N:3]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:14]1([C:6]2[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[C:2]([N:33]3[CH2:34][CH2:35][N:30]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=4)[CH2:31][CH2:32]3)[N:3]=[C:4]([C:20]([F:23])([F:22])[F:21])[N:5]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 944591-(2-Pyridyl)piperazineHCID 104046804-Chloro-5,6-diphenyl-2-(trifluoromethyl)pyrimidine

Product 1

HCID 249590264,5-Diphenyl-6-(4-pyridin-2-yl-piperazin-1-yl)-2-(trifluoromethyl)pyrimidineYield 69.66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
28 °C

Procedure

To a solution of 4-chloro-5,6-diphenyl-2-(trifluoromethyl)pyrimidine (0.5 g, 1.49 mmol, prepared according to the procedure described in PCT/IB03/02879) in dimethylformamide (5 ml) was added 1-pyridin-2-yl piperazine (0.107 g, 0.66 mmol) and anhydrous potassium carbonate (0.2 g) under stirring at 28° C. The reaction mixture was stirred for 4 hours and when TLC conformed the completion, it was poured onto ice. The solid thus obtained was filtered and washed with water (20 ml). The above solid was then dissolved in dichloromethane (50 ml) and dried over anhydrous sodium sulphate. Evaporation of the solvent afforded the title compound (0.48 g, yield 69.66%, purity by HPLC 99.8%). m.p. 165-167° C. 1H-NMR (CDCl3) δ: 3.43 (s, 8H), 6.58-6.64 (m, 2H), 7.14-7.21 (m, 7H), 7.26-7.29 (m, 3H), 7.45-7.49 (t, 1H), 8.14-8.15 (d, 1H). IR cm−1 (KBr): 3436, 2839, 1591, and 1557. MS m/z: 462.1 (M++1).

Workup

  1. stirringThe reaction mixture was stirred for 4 hours
  2. additionwas poured onto ice
  3. customThe solid thus obtained
  4. filtrationwas filtered
  5. washwashed with water (20 ml)
  6. dissolutionThe above solid was then dissolved in dichloromethane (50 ml)
  7. dry with materialdried over anhydrous sodium sulphate
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-169caa3c7c6849d4adc7fceaaa246f71
Source dataset
uspto-grants-2011_01
Patent number
US07863446B2

Reaction notes

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