4-(4-Bromopyrimidin-2-yl)morpholine → HCID 86696145, compound

HRID 1528652Notes

Reaction equation

HRID 1528652 reaction equation
[OH:1][C:2]([CH3:35])([CH3:34])[CH2:3][C@@:4]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16](B3OC(C)(C)C(C)(C)O3)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1.Br[C:37]1[CH:42]=[CH:41][N:40]=[C:39]([N:43]2[CH2:48][CH2:47][O:46][CH2:45][CH2:44]2)[N:38]=1>>[OH:1][C:2]([CH3:35])([CH3:34])[CH2:3][C@@:4]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:14]=[CH:15][C:16]([C:41]3[CH:42]=[CH:37][N:38]=[C:39]([N:43]4[CH2:48][CH2:47][O:46][CH2:45][CH2:44]4)[N:40]=3)=[CH:17][CH:18]=2)[CH3:12])[CH2:6][CH2:5]1

Participants

3

Reactant 2

HCID 457874954-(4-Bromopyrimidin-2-yl)morpholineHCID 59532385(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one

Product 1

HCID 86696145HCID 86696145, compound

Procedure

The title compound was prepared from (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-{(S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl}-1,3-oxazinan-2-one and 4-(4-bromopyrimidin-2-yl)morpholine following a procedure analogous to that described in Example 35. LC (method 5): tR=1.15 min; Mass spectrum (ESI+): m/z=517 [M+H]+; 1H NMR (CD3OD) δ 0.95 (s, 3H), 1.25 (s, 3H), 1.58 (d, 3H), 2.17 (s, 2H), 2.30 (m, 1H), 2.50 (m, 2H), 3.15 (m, 1H), 3.29 (m, 4H), 3.84 (m, 4H), 5.59 (q, 1H), 7.05 (d, 1H), 7.12 (d, 2H), 7.25-7.40 (5H), 7.94 (d, 2H), 8.17 (d, 1H).

Sources & evidence

ORD record
ord-17409f5462e04b88b96cad70c59555c5
Source dataset
uspto-grants-2015_07
Patent number
US09090605B2

Reaction notes

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