HCID 57468596, compound → HCID 24760586, compound

HRID 1928354Notes

Reaction equation

HRID 1928354 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=3)[N:9]=2)[CH:5]=[C:4]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[CH:3]=1.[H][H]>C1COCC1.CCO.[Pd]>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]3[CH:15]=[C:16]([NH2:20])[CH:17]=[CH:18][CH:19]=3)[N:9]=2)[CH:5]=[C:4]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:25][CH:24]=2)[CH:3]=1

Participants

5

Reactant 2

HCID 57468596HCID 57468596, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 24760586HCID 24760586, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A mixture of 4-[6-methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-2-(3-nitro-phenyl)-pyrimidine (example 322) (2.1 g, 4.81 mmol) in THF-EtOH 1:1 (100 mL) and 10% palladium on carbon (1 mol %) was hydrogenated (1 bar hydrogen) at 23° C. for 2 h. The catalyst was filtered off, washed with EtOH and the filtrate was completely evaporated totally to leave a crude product, which was purified by silica gel column chromatography with heptane/EtOAc, followed by trituration with diethyl ether to give the title compound as an off-white solid (1.5 g, 76%). MS (ISP) 407.4 [(M+H)+]; mp 167° C.

Workup

  1. customat 23° C.
  2. customfor 2 h
  3. filtrationThe catalyst was filtered off
  4. washwashed with EtOH
  5. customthe filtrate was completely evaporated totally
  6. customto leave a crude product, which
  7. customwas purified by silica gel column chromatography with heptane/EtOAc

Sources & evidence

ORD record
ord-222bdc5bac7f456da4f63dbaa32ab0cf
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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