2,4-Dichloropyrimidine → 3-(2-Chloropyrimidin-4-yl)-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine

HRID 1796012Notes

Reaction equation

HRID 1796012 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[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>>[Cl:1][C:2]1[N:7]=[C:6]([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)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 775312,4-DichloropyrimidineHCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-

Product 1

HCID 98574753-(2-Chloropyrimidin-4-yl)-7-(trifluoromethyl)imidazo[1,2-a]pyrimidineYield 39.8%

Procedure

2,4-Dichloropyrimidine (317 mg, 2.13 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (1.4 mmol) by the method of Example 1 to give 3-(2-chloropyrimidin-4-yl)-7-trifluoromethylimidazo[1,2-α]pyrimidine (167 mg) as a white solid: δH (400 MHz, DMSO) 7.91 (1H, d, J 7), 8.25 (1H, d, J 5), 8.83 (1H, d, J 5), 9.17 (1H, s), 10.22 (1H, d, J 7); m/z (ES+) 300, 302 (M++H).

Sources & evidence

ORD record
ord-d3ed14230be943d19a782b86b4930890
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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