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

HRID 1966338
Notes
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Reaction equation

HRID 1966338 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=O)C>[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 6228Dimethylformamide
Solvent

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 DMF (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 confirmed 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-0a346fb59ff0466d8eb47a7d2c4c48fe
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08420653B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes