Hexane → 4-(4-Chloro-phenyl)-2-[4-(3-methanesulfonyl-phenyl)-imidazol-1-yl]-6-methyl-pyrimidine

HRID 1928230Notes

Reaction equation

HRID 1928230 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([N:15]3[CH:19]=[C:18]([Sn](CCCC)(CCCC)CCCC)[N:17]=[CH:16]3)[N:9]=2)=[CH:4][CH:3]=1.BrC1C=C([CH2:40][S:41](CC2C=CC=C(Br)C=2)(=[O:43])=[O:42])C=CC=1.[CH3:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([N:15]3[CH:19]=[C:18]([C:54]4[CH:53]=[CH:52][CH:57]=[C:56]([S:41]([CH3:40])(=[O:43])=[O:42])[CH:55]=4)[N:17]=[CH:16]3)[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 534433923-Bromophenylmethyl sulphoneHCID 574688274-(4-Chloro-phenyl)-6-methyl-2-(4-tributylstannanyl-imidazol-1-yl)-pyrimidine

Product 1

HCID 574689774-(4-Chloro-phenyl)-2-[4-(3-methanesulfonyl-phenyl)-imidazol-1-yl]-6-methyl-pyrimidineYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of 4-(4-chloro-phenyl)-6-methyl-2-(4-tributylstannanyl-imidazol-1-yl)-pyrimidine (Example G.3) (0.47 g, 0.84 mmol), commercially available 3-bromo-phenylmethyl sulfone (0.22 g, 0.92 mmol), tetrakis(triphenyl-phosphine)palladium (0.058 g, 0.05 mmol) in toluene (8 mL) was heated under reflux conditions for 15 h. Hexane (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 (0.33 g, 92%) as an off-white solid. MS (ISN) 423.3 [(M−H)−]; mp 233° 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-a9d6410ffedd4859a23c20ba019377a8
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

Loading…