2-Bromo-6-morpholinopyridine → HCID 10132526, compound

HRID 1796068Notes

Reaction equation

HRID 1796068 reaction equation
Br[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:19]1[N:23]2[CH:24]=[CH:25][C:26]([C:28]([F:31])([F:30])[F:29])=[N:27][C:22]2=[N:21][CH:20]=1)CCC>>[N:8]1([C:6]2[N:7]=[C:2]([C:19]3[N:23]4[CH:24]=[CH:25][C:26]([C:28]([F:29])([F:30])[F:31])=[N:27][C:22]4=[N:21][CH:20]=3)[CH:3]=[CH:4][CH:5]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 71645992-Bromo-6-morpholinopyridineHCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-

Product 1

HCID 10132526HCID 10132526, compoundYield 35%

Procedure

4-(6-Bromopyridin-2-yl)morpholine (0.46 g, 1.9 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (1.8 mmol) by the method of Example 1. Purification by chromatography on silica gel eluting with dichloromethane on a gradient of methanol (0-10%) and crystallisation from ethyl acetate-isohexane gave 3-[6-(morpholin-4-yl)pyridin-2-yl]-7-trifluoromethylimidazo[1,2-α]pyrimidine (220 mg) as a yellow solid: δH (400 MHz, CDCl3) 3.57 (4H, t, J 5), 3.90 (4H, t, J 5), 6.65 (1H, d, J 8), 7.20 (1H, d, J 8), 7.33 (1H, d, J 7), 7.65 (1H, dd, J 8 and 8), 8.42 (1H, s), 10.19 (1H, d, J 7); m/z (ES+) 350 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane
  2. customon a gradient of methanol (0-10%) and crystallisation from ethyl acetate-isohexane

Sources & evidence

ORD record
ord-34bf9e06748141829a790696a5d761a6
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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