5-Bromo-2-cyclopropylpyrimidine → 3-{(S)-1-[4-(2-Cyclopropyl-pyrimidin-5-yl)-phenyl]-ethyl}-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one

HRID 1046247Notes

Reaction equation

HRID 1046247 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:38]=[N:39][C:40]([CH:43]2[CH2:45][CH2:44]2)=[N:41][CH:42]=1>>[CH:43]1([C:40]2[N:41]=[CH:42][C:37]([C:16]3[CH:15]=[CH:14][C:13]([C@@H:11]([N:7]4[CH2:6][CH2:5][C@:4]([CH2:3][C:2]([OH:1])([CH3:34])[CH3:35])([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[O:9][C:8]4=[O:10])[CH3:12])=[CH:18][CH:17]=3)=[CH:38][N:39]=2)[CH2:45][CH2:44]1

Participants

3

Reactant 2

HCID 204444135-Bromo-2-cyclopropylpyrimidineHCID 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 584853063-{(S)-1-[4-(2-Cyclopropyl-pyrimidin-5-yl)-phenyl]-ethyl}-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one

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 5-bromo-2-cyclopropyl-pyrimidine (for preparation see WO 2006004532) following a procedure analogous to that described in Example 171. Mass spectrum (ESI+): m/z=472 [M+H]+.

Sources & evidence

ORD record
ord-43ba1c98e62c44d18c4eaf248f70e753
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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