Potassium Carbonate → 2-(Pyrrolidin-1-yl)-4-(trifluoromethyl)-N-[[4-(trifluoromethyl)phenyl]methyl]pyrimidine-5-carboxamide

HRID 24284

Reaction equation

HRID 24284 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12](Cl)=[O:13])=[CH:4][N:3]=1.C(=O)(O)[O-].[Na+].[F:20][C:21]([F:31])([F:30])[C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[NH:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1>ClCCl>[N:38]1([C:2]2[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]([NH:27][CH2:26][C:25]3[CH:28]=[CH:29][C:22]([C:21]([F:30])([F:31])[F:20])=[CH:23][CH:24]=3)=[O:13])=[CH:4][N:3]=2)[CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 768044-(Trifluoromethyl)benzylamineHCID 516892Sodium BicarbonateHCID 27367082-Chloro-4-(trifluoromethyl)pyrimidine-5-carbonyl chloride

Product 1

HCID 98882572-(Pyrrolidin-1-yl)-4-(trifluoromethyl)-N-[[4-(trifluoromethyl)phenyl]methyl]pyrimidine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-4-(trifluoromethyl)pyrimidine-5-carbonyl chloride (0.74 g, 3.0 mmol) in dichloromethane (5 mL), was added saturated sodium bicarbonate (5 mL) and 4-(trifluoromethyl)benzylamine (0.58 g, 3.3 mmol). The reaction mixture was stirred at room temperature for 3 hours. The precipitated white solid of 2-chloro-4-(trifluoromethyl)-N-[[4-(trifluoromethyl)phenyl]methyl]pyrimidine-5-carboxamide was collected by filtration and then dissolved in acetonitrile (10-15 mL). Potassium carbonate (0.62 g, 4.5 mmol) and pyrrolidine (0.43 g, 6 mmol)) were added. The reaction mixture was stirred at room temperature overnight. The inorganic salts were filtered off and the filtrate was concentrated in vacuo to provide the pure titled compound: MS m/e 419 (MH+). 1H NMR (DMSO-d6): δ 9.10 (t, J=5.9 Hz, 1H), 8.68 (s, 1H), 7.71 (d, J=8.1 Hz, 2H), 7.55 (d, J=8.0 Hz, 2H), 4.51 (d, J=6.1 Hz, 2H), 3.5-3.55 (m, br, 4H), 1.93-1.98 (m, 4H).

Workup

  1. filtrationThe precipitated white solid of 2-chloro-4-(trifluoromethyl)-N-[[4-(trifluoromethyl)phenyl]methyl]pyrimidine-5-carboxamide was collected by filtration
  2. dissolutiondissolved in acetonitrile (10-15 mL)
  3. stirringThe reaction mixture was stirred at room temperature overnight
  4. filtrationThe inorganic salts were filtered off
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b4d1483621df437a9277198972c5d0dc
Source dataset
uspto-grants-2005_02
Patent number
US06855829B2

Linked notes

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