Heptane → 2-[4-(3-Methanesulfonyl-phenyl)-imidazol-1-yl]-4-trifluoromethyl-6-(4-trifluoromethylphenyl)-pyrimidine

HRID 1928242Notes

Reaction equation

HRID 1928242 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[N:7]=[CH:8][N:9]([C:11]2[N:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)[N:12]=2)[CH:10]=1)CCC.BrC1C=C([CH2:46][S:47](CC2C=CC=C(Br)C=2)(=[O:49])=[O:48])C=CC=1.C[CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64]>C1(C)C=CC=CC=1>[CH3:46][S:47]([C:64]1[CH:63]=[C:62]([C:6]2[N:7]=[CH:8][N:9]([C:11]3[N:16]=[C:15]([C:17]([F:18])([F:19])[F:20])[CH:14]=[C:13]([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:30])[F:29])=[CH:23][CH:22]=4)[N:12]=3)[CH:10]=2)[CH:61]=[CH:60][CH:59]=1)(=[O:49])=[O:48]

Participants

5

Reactant 3

HCID 8900HeptaneHCID 534433923-Bromophenylmethyl sulphoneHCID 574688252-(4-Tributylstannanyl-imidazol-1-yl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidine

Product 1

HCID 574689892-[4-(3-Methanesulfonyl-phenyl)-imidazol-1-yl]-4-trifluoromethyl-6-(4-trifluoromethylphenyl)-pyrimidineYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of 2-(4-tributylstannanyl-imidazol-1-yl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidine (Example G.1) (0.155 g, 0.24 mmol), commercially available 3-bromo-phenylmethyl sulfone (0.062 g, 0.26 mmol), tetrakis(triphenyl-phosphine)palladium (0.017 g, 0.015 mmol) in toluene (5 mL) was heated under reflux conditions for 15 h. Heptane (5 mL) was added at room temperature and the mixture was stirred for 1 h. The precipitate was collected by filtration, washed with heptane and dried. Further purification by flash chromatography on silica gel (ethyl acetate/heptane) and crystallization (dichloromethane/hexane) yielded the title compound (0.078 g, 64%) as a white solid. MS (ISP) 512.9 [(M+H)+]; mp 231° C.

Workup

  1. temperaturewas heated under reflux conditions for 15 h
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with heptane
  4. customdried
  5. customFurther purification by flash chromatography
  6. customon silica gel (ethyl acetate/heptane) and crystallization (dichloromethane/hexane)

Sources & evidence

ORD record
ord-585b845ea2e046309c9b393e97c02dbf
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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