Tetrahydrofuran → HCID 60209449, compound

HRID 1928244Notes

Reaction equation

HRID 1928244 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]3[N:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=4)[N:17]=3)[CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.C1COCC1>CO.[Pd]>[F:25][C:22]([F:23])([F:24])[C:20]1[CH:19]=[C:18]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)[N:17]=[C:16]([C:12]2[CH:11]=[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([NH2:1])[CH:5]=3)[CH:15]=[CH:14][CH:13]=2)[N:21]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 57468992HCID 57468992, compound

Product 1

HCID 60209449HCID 60209449, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred suspension of 2-(3′-nitro-biphenyl-3-yl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidine (1.6 g, 3.27 mmol) in MeOH (40 mL) was added at room temperature Pd—C (10%, 0.16 g) and THF (40 mL). The mixture was stirred at room temperature under H2 atmosphere for 2 h, the catalyst was removed by filtration and the obtained solution evaporated. The crude product was further purified by crystallization from diethyl ether/hexane to yield the title compound as an off-white solid (1.28 g, 85%). MS (ISP) 460.2 [(M+H)+]; mp 156.5° C.

Workup

  1. customthe catalyst was removed by filtration
  2. customthe obtained solution evaporated
  3. customThe crude product was further purified by crystallization from diethyl ether/hexane

Sources & evidence

ORD record
ord-ebfa819229d945a2b940ef7132fffa9e
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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