(2-Bromophenyl)(morpholino)methanone → 5-{5-[2-(Morpholin-4-ylcarbonyl)phenyl]pyridin-2-yl}pyrimidin-2-amine

HRID 1524103Notes

Reaction equation

HRID 1524103 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[C:30]([N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1)=[O:31]>>[N:32]1([C:30]([C:25]2[CH:24]=[CH:29][CH:28]=[CH:27][C:26]=2[C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[N:19][C:18]([NH2:21])=[N:17][CH:16]=3)=[N:13][CH:14]=2)=[O:31])[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1

Participants

3

Reactant 2

HCID 532184(2-Bromophenyl)(morpholino)methanoneHCID 903141215-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pyrimidin-2-amine

Product 1

HCID 903141805-{5-[2-(Morpholin-4-ylcarbonyl)phenyl]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 (2-bromophenyl)(morpholino)methanone. MS (ESI): mass calcd. for C20H19N5O2, 361.15; m/z found, 362.1 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.96 (s, 2H), 8.69-8.64 (m, 1H), 7.95-7.87 (m, 2H), 7.64-7.59 (m, 1H), 7.58-7.51 (m, 2H), 7.49-7.42 (m, 1H), 3.69-3.54 (m, 3H), 3.48-3.33 (m, 2H), 3.20-3.07 (m, 1H), 2.97-2.80 (m, 2H).

Sources & evidence

ORD record
ord-8041cce0a5c04eeda663b80b2efcdce0
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

Loading…