Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → HCID 10269115, compound

HRID 1796090Notes

Reaction equation

HRID 1796090 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)[N:3]=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>>[S:10]1[CH:11]=[CH:12][C:8]([C:4]2[N: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:9]1

Participants

3

Reactant 2

HCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-HCID 221807762-Bromo-6-(thiophen-3-yl)pyridine

Product 1

HCID 10269115HCID 10269115, compoundYield 11.2%

Procedure

2-Bromo-6-(thien-3-yl)pyridine (2.20 g, 9.1 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (9.0 mmol) by the method of Example 1. Purification by chromatography on silica gel eluting with isohexane on a gradient of ethyl acetate (10-80%) and trituration with isohexane followed by crystallisation from ethyl acetate-isohexane gave 3-[6-(thien-3-yl)pyridin-2-yl]-7-trifluoromethyl-imidazo[1,2-α]pyrimidine (350 mg) as a pale yellow solid: δH (400 MHz, CDCl3) 7.40 (1H, d, J 7), 7.48-7.50 (1H, m), 7.60 (1H, d, J 8), 7.69-7.73 (2H, m), 7.86 (1H, dd, J 8 and 8), 7.92-7.94 (1H, m), 8.54 (1H, s), 10.56 (1H, d, J 7); m/z (ES+) 347 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with isohexane on a gradient of ethyl acetate (10-80%) and trituration with isohexane
  2. customfollowed by crystallisation from ethyl acetate-isohexane

Sources & evidence

ORD record
ord-30be7184a9004b85b3ec0f35038945b3
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

Loading…