Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → 3-[3-([1,2,4]Triazol-1-yl)-phenyl]-7-trifluoromethylimidazo[1,2-a]pyrimidine

HRID 478249Notes

Reaction equation

HRID 478249 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[N:11][CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:18]1[N:22]2[CH:23]=[CH:24][C:25]([C:27]([F:30])([F:29])[F:28])=[N:26][C:21]2=[N:20][CH:19]=1)CCC>>[N:8]1([C:4]2[CH:3]=[C:2]([C:18]3[N:22]4[CH:23]=[CH:24][C:25]([C:27]([F:28])([F:29])[F:30])=[N:26][C:21]4=[N:20][CH:19]=3)[CH:7]=[CH:6][CH:5]=2)[CH:12]=[N:11][CH:10]=[N:9]1

Participants

3

Reactant 2

HCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-HCID 223294981-(3-bromophenyl)-1H-1,2,4-triazole

Product 1

HCID 98805743-[3-([1,2,4]Triazol-1-yl)-phenyl]-7-trifluoromethylimidazo[1,2-a]pyrimidine

Procedure

1-(3-Bromophenyl)-1H-[1,2,4]triazole (1.7 g, 7.6 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-a]pyrimidine (3.8 mmol) by the method of Example 32. Purification by chromatography on silica gel eluting with dichloromethane on a gradient of methanol (1-3%), then crystallisation from toluene/isohexane, gave 3-[3-([1,2,4]triazol-1-yl)-phenyl]-7-trifluoromethylimidazo[1,2-a]pyrimidine as an off-white solid: δH (400 MHz, DMSO) 9.43 (1H, d, J 7), 9.41 (1H, s), 8.38 (1H, s), 8.30 (1H, s), 8.26-8.28 (1H, m), 7.97-8.00 (1H, m), 7.76-7.81 (2H, m), 7.56 (1H, d, J 7); m/z (ES+) 331 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane on a gradient of methanol (1-3%)
  2. customcrystallisation from toluene/isohexane

Sources & evidence

ORD record
ord-c8aaa1f10b2d427fb80d06ff7999e7e2
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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