2-Bromoanisole → 5-[5-(2-Methoxyphenyl)pyridin-2-yl]pyrimidin-2-amine

HRID 1524104Notes

Reaction equation

HRID 1524104 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:16]=[N:17][C:18]([NH2:21])=[N:19][CH:20]=3)=[N:13][CH:14]=2)O1.Br[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH3:31]>>[CH3:31][O:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[N:19][C:18]([NH2:21])=[N:17][CH:16]=2)=[N:13][CH:14]=1

Participants

3

Reactant 2

HCID 113582-BromoanisoleHCID 903141215-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pyrimidin-2-amine

Product 1

HCID 903138495-[5-(2-Methoxyphenyl)pyridin-2-yl]pyrimidin-2-amine

Procedure

The title compound was prepared in a manner similar to that described in Example 427 using 5-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pyrimidin-2-amine and 1-bromo-2-methoxybenzene. MS (ESI): mass calcd. for C16H14N4O. C2HF3O2, 278.12; m/z found, 279.1 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 9.00 (s, 2H), 8.81 (d, J=2.2, 1H), 8.28 (dd, J=8.4, 2.2, 1H), 8.02 (d, J=8.4, 1H), 7.48-7.41 (m, 2H), 7.16 (d, J=8.4, 1H), 7.11 (m, 1H), 3.87 (s, 3H).

Sources & evidence

ORD record
ord-8278e046b60144a6aba05fdf2de5d3ad
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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