Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → 3-(6-Isopropoxypyridin-2-yl)-7-(trifluoromethyl)imidazo[1,2-alpha]pyrimidine

HRID 1796081Notes

Reaction equation

HRID 1796081 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH:9]([CH3:11])[CH3:10])[N:3]=1.C([Sn](CCCC)(CCCC)[C:17]1[N:21]2[CH:22]=[CH:23][C:24]([C:26]([F:29])([F:28])[F:27])=[N:25][C:20]2=[N:19][CH:18]=1)CCC>>[CH:9]([O:8][C:4]1[N:3]=[C:2]([C:17]2[N:21]3[CH:22]=[CH:23][C:24]([C:26]([F:27])([F:28])[F:29])=[N:25][C:20]3=[N:19][CH:18]=2)[CH:7]=[CH:6][CH:5]=1)([CH3:11])[CH3:10]

Participants

3

Reactant 2

HCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-HCID 221807682-Bromo-6-isopropoxypyridine

Product 1

HCID 98801833-(6-Isopropoxypyridin-2-yl)-7-(trifluoromethyl)imidazo[1,2-alpha]pyrimidineYield 35.7%

Procedure

2-Bromo-6-isopropoxypyridine (0.32 g, 1.58 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (1.13 mmol) by the method of Example 1. Purification by chromatography on silica gel eluting with isohexane on a gradient of ethyl acetate (20-40%) and trituration with isohexane gave 3-(6-isopropoxypyridin-2-yl)-7-(trifluoromethyl)imidazo[1,2-α]pyrimidine (130 mg) as a pale yellow solid: δH (400 MHz, CDCl3) 1.45 (6H, d, J 6), 5.29 (1H, quin, J 6), 6.69 (1H, d, J 8), 7.34 (1H, d, J 7), 7.39 (1H, d, J 7), 7.70 (1H, dd, J 8 and 7), 8.46 (1H, s), 10.26 (1H, d, J 7); m/z (ES+) 323 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with isohexane on a gradient of ethyl acetate (20-40%) and trituration with isohexane

Sources & evidence

ORD record
ord-a06bb98f839a4cc1a266ea61907af0bb
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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