Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → HCID 10109084, compound

HRID 2183976Notes

Reaction equation

HRID 2183976 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:14])=[C:6]([C:8]2[CH:13]=[N:12][CH:11]=[CH:10][N:9]=2)[CH:7]=1.C([Sn](CCCC)(CCCC)[C:20]1[N:24]2[CH:25]=[CH:26][C:27]([C:29]([F:32])([F:31])[F:30])=[N:28][C:23]2=[N:22][CH:21]=1)CCC>>[F:14][C:5]1[CH:4]=[CH:3][C:2]([C:20]2[N:24]3[CH:25]=[CH:26][C:27]([C:29]([F:30])([F:31])[F:32])=[N:28][C:23]3=[N:22][CH:21]=2)=[CH:7][C:6]=1[C:8]1[CH:13]=[N:12][CH:11]=[CH:10][N:9]=1

Participants

3

Reactant 2

HCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-HCID 22473569HCID 22473569, compound

Product 1

HCID 10109084HCID 10109084, compound

Procedure

2-(5-Bromo-2-fluorophenyl)pyrazine was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine by the method of Example 32. Purification by chromatography on silica gel eluting with dichloromethane containing 4% methanol followed by crystallisation from hot toluene gave 3-[4-fluoro-3-(pyrazin-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine: δH (400 MHz, DMSO) 9.31 (1H, d, J 7), 9.14 (1H, m), 8.85 (1H, dd, J 2 and 1.5), 8.73 (1H, d, J 2), 8.32 (1H, s), 8.27 (1H, dd, J 7 and 2), 7.96 (1H, m), 7.68 (1H, dd, J 11 and 9), 7.54 (1H, d, J 7); m/z (ES+) 360 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane containing 4% methanol
  2. customfollowed by crystallisation from hot toluene

Sources & evidence

ORD record
ord-47ebe26edfe04e289a4d0e8dc308fffa
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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