2-Bromo-5-methylpyridine → HCID 9878740, compound

HRID 1796022Notes

Reaction equation

HRID 1796022 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:14]1[N:18]2[CH:19]=[CH:20][C:21]([C:23]([F:26])([F:25])[F:24])=[N:22][C:17]2=[N:16][CH:15]=1)CCC>>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:14]2[N:18]3[CH:19]=[CH:20][C:21]([C:23]([F:24])([F:25])[F:26])=[N:22][C:17]3=[N:16][CH:15]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 5642162-Bromo-5-methylpyridineHCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-

Product 1

HCID 9878740HCID 9878740, compound

Procedure

2-Bromo-5-methylpyridine (1.29 g, 7.5 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (3.8 mmol) by the method of Example 1. Purification by chromatography on silica gel eluting with dichloromethane containing 1% methanol, then crystallisation from toluene/isohexane, gave 3-(5-methylpyridin-2-yl)-7-trifluoromethyl-imidazo[1,2-α]pyrimidine as a yellow solid: δH (400 MHz, CDCl3) 10.48 (1H, d, J 7), 8.50-8.52 (1H, m), 8.46 (1H, s), 7.72 (1H, d, J 8), 7.61-7.65 (1H, m), 7.31 (1H, d, J 7); m/z (ES+) 279 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane containing 1% methanol
  2. customcrystallisation from toluene/isohexane

Sources & evidence

ORD record
ord-ea248403323d4d58abe537e3c7e835be
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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