HCID 67324535, compound → HCID 67325540, compound

HRID 1854629Notes

Reaction equation

HRID 1854629 reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([CH3:15])[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:21]1[S:25][C:24]([C:26]2[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=2)[C:29]#[N:30])=[N:23][CH:22]=1)CCC>>[CH3:15][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([NH:8][C:6]2[N:7]=[C:2]([C:21]3[S:25][C:24]([C:26]4[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=4)[C:29]#[N:30])=[N:23][CH:22]=3)[CH:3]=[CH:4][CH:5]=2)[N:14]=1

Participants

3

Reactant 2

HCID 67324535HCID 67324535, compoundHCID 86676503HCID 86676503, compound

Product 1

HCID 67325540HCID 67325540, compound

Procedure

By following essentially the same procedure in preparative example 019 and starting with N-(6-bromopyridin-2-yl)-4-methylpyrimidin-2-amine (215 mg 0.81 mmol) and 3-(5-(tributylstannyl)thiazol-2-yl)benzonitrile (656 mg, 1.38 mmol), the 3-(5-(6-(4-methylpyrimidin-2-ylamino)pyridin-2-yl)thiazol-2-yl)benzonitrile was obtained and purified by dry flash chromatography over SiO2 eluting with DCM/MeOH (5%)/NEt3 (0.5%), by precipitation in DCM/MeOH and by trituration with Et2O (119 mg, 39%). 1H NMR (300 MHz, DMSO-d6) δ 9.60 (br s, 1H), 8.62 (s, 1H), 8.43 (d, J=5.0 Hz, 1H), 8.38 (d, J=2.3 Hz, 1H), 8.31-8.23 (m, 2H), 8.01-7.95 (m, 1H), 7.86 (t, J=8.0 Hz, 1H), 7.75 (t, J=7.9 Hz, 1H), 7.64 (d, J=7.5 Hz, 1H), 6.89 (d, J=5.0 Hz, 1H), 2.42 (s, 3H). (APCI+) m/z 371 (M+H)+.

Sources & evidence

ORD record
ord-76e5634d50be4549920e5530b7687d9d
Source dataset
uspto-grants-2015_02
Patent number
US08962665B2

Reaction notes

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