2-(2-Bromophenoxy)pyrimidine → 6-Amino-3-[3-fluoro-2'-(pyrimidin-2-yloxy)biphenyl-4-yl]pyrazine-2-carbonitrile

HRID 1524148Notes

Reaction equation

HRID 1524148 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([C:10]2[CH:15]=[CH:14][C:13](B3OC(C)(C)C(C)(C)O3)=[CH:12][C:11]=2[F:25])=[N:4][CH:3]=1.Br[C:27]1[CH:39]=[CH:38][CH:37]=[CH:36][C:28]=1[O:29][C:30]1[N:35]=[CH:34][CH:33]=[CH:32][N:31]=1>>[NH2:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([C:10]2[CH:15]=[CH:14][C:13]([C:27]3[CH:39]=[CH:38][CH:37]=[CH:36][C:28]=3[O:29][C:30]3[N:31]=[CH:32][CH:33]=[CH:34][N:35]=3)=[CH:12][C:11]=2[F:25])=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 145311902-(2-Bromophenoxy)pyrimidineHCID 90312891HCID 90312891, compound

Product 1

HCID 903151486-Amino-3-[3-fluoro-2'-(pyrimidin-2-yloxy)biphenyl-4-yl]pyrazine-2-carbonitrile

Procedure

The title compound was prepared using conditions analogous to those used to make Example 6 utilizing 6-amino-3-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazine-2-carbonitrile and 2-(2-bromophenoxy)pyrimidine. MS (ESI): mass calcd. for C21H13FN6O, 384.11; m/z found, 385.0 [M+H]+. 1H NMR (600 MHz, DMSO-δ6) δ 8.55 (d, J=4.8, 2H), 8.20 (s, 1H), 7.61 (dd, J=7.7, 1.7, 1H), 7.57-7.49 (m, 2H), 7.44-7.37 (m, 3H), 7.35 (s, 2H), 7.32 (dd, J=8.1, 1.2, 1H), 7.19-7.15 (m, 1H).

Sources & evidence

ORD record
ord-1a941064e79c408b9a39b15ce2fe13cd
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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