2-(2-Bromophenoxy)pyrimidine → 5-[3-Fluoro-2'-(pyrimidin-2-yloxy)biphenyl-4-yl]pyrimidin-2-amine

HRID 1524024Notes

Reaction equation

HRID 1524024 reaction equation
Br[C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][C:5]1[N:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[F:15][C:16]1[CH:21]=[C:20](B2OC(C)(C)C(C)(C)O2)[CH:19]=[CH:18][C:17]=1[C:31]1[CH:32]=[N:33][C:34]([NH2:37])=[N:35][CH:36]=1>>[F:15][C:16]1[CH:21]=[C:20]([C:2]2[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=2[O:4][C:5]2[N:10]=[CH:9][CH:8]=[CH:7][N:6]=2)[CH:19]=[CH:18][C:17]=1[C:31]1[CH:36]=[N:35][C:34]([NH2:37])=[N:33][CH:32]=1

Participants

3

Reactant 2

HCID 145311902-(2-Bromophenoxy)pyrimidineHCID 903131425-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine

Product 1

HCID 903149385-[3-Fluoro-2'-(pyrimidin-2-yloxy)biphenyl-4-yl]pyrimidin-2-amine

Procedure

The title compound was prepared in a manner similar to that described in Example 88 using 2-(2-bromophenoxy)pyrimidine and 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine. MS (ESI): mass calcd. for C20H14FN5O, 359.12; m/z found, 360.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 8.58 (d, J=4.8, 2H), 8.43 (d, J=1.4, 2H), 7.58-7.46 (m, 3H), 7.42-7.27 (m, 4H), 7.20 (t, J=4.8, 1H), 6.88 (s, 2H).

Sources & evidence

ORD record
ord-56d3f724727341858ba729848dc04518
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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