Heptane → 4-(3,4-Dichloro-phenyl)-2-[4-(3-methanesulfonyl-phenyl)-imidazol-1-yl]-6-methyl-pyrimidine

HRID 1928237Notes

Reaction equation

HRID 1928237 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([N:16]3[CH:20]=[C:19]([Sn](CCCC)(CCCC)CCCC)[N:18]=[CH:17]3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].BrC1C=C([CH2:41][S:42](CC2C=CC=C(Br)C=2)(=[O:44])=[O:43])C=CC=1.C[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([N:16]3[CH:20]=[C:19]([C:55]4[CH:56]=[CH:57][CH:58]=[C:59]([S:42]([CH3:41])(=[O:44])=[O:43])[CH:54]=4)[N:18]=[CH:17]3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 8900HeptaneHCID 534433923-Bromophenylmethyl sulphoneHCID 57468828HCID 57468828, compound

Product 1

HCID 574689844-(3,4-Dichloro-phenyl)-2-[4-(3-methanesulfonyl-phenyl)-imidazol-1-yl]-6-methyl-pyrimidineYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of 4-(3,4-dichloro-phenyl)-6-methyl-2-(4-tributylstannanyl-imidazol-1-yl)-pyrimidine (Example G.4) (0.45 g, 0.76 mmol), commercially available 3-bromo-phenylmethyl sulfone (0.20 g, 0.83 mmol), tetrakis(triphenyl-phosphine)palladium (0.053 g, 0.046 mmol) in toluene (8 mL) was heated under reflux conditions for 15 h. Heptane (10 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 to yield the title compound (0.27 g, 78%) as an off-white solid. MS (ISP) 459.2 [(M+H)+]; mp 213° C.

Workup

  1. temperaturewas heated under reflux conditions for 15 h
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with heptane
  4. customdried

Sources & evidence

ORD record
ord-841a0647ca684bf5941138d75787c718
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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