5-(2-Chlorophenyl)pyrimidin-2-amine → 5-{2-[6-(2-Aminopyrimidin-5-yl)-5-fluoropyridin-3-yl]phenyl}pyrimidin-2-amine

HRID 1524171Notes

Reaction equation

HRID 1524171 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11](B(O)O)=[CH:10][C:9]=2[F:17])=[CH:4][N:3]=1.Cl[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[CH:26]=[N:27][C:28]([NH2:31])=[N:29][CH:30]=1>>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]3[CH:26]=[N:27][C:28]([NH2:31])=[N:29][CH:30]=3)=[CH:10][C:9]=2[F:17])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 665201295-(2-Chlorophenyl)pyrimidin-2-amineHCID 90313056(6-(2-Aminopyrimidin-5-yl)-5-fluoropyridin-3-yl)boronic acid

Product 1

HCID 903134875-{2-[6-(2-Aminopyrimidin-5-yl)-5-fluoropyridin-3-yl]phenyl}pyrimidin-2-amine

Procedure

The title compound was prepared in a manner similar to that described in Example 427 using (6-(2-aminopyrimidin-5-yl)-5-fluoropyridin-3-yl)boronic acid and 5-(2-chlorophenyl)pyrimidin-2-amine. MS (ESI): mass calcd. for C19H14FN7, 359.13; m/z found, 360.1 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.93 (s, 2H), 8.31-8.28 (m, 1H), 8.19 (s, 2H), 7.64 (dd, J=12.0, 1.9, 1H), 7.59-7.51 (m, 4H).

Sources & evidence

ORD record
ord-85f4c0f703fa48c8924a5ef65b4788aa
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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