5-Bromo-2-methylpyrimidine → HCID 49838824, compound

HRID 2368055Notes

Reaction equation

C1([C@@H](C2C=CC(B3OC(C)(C)C(C)(C)O3)=CC=2)N2CC[C@](CC(O)(C)C)(C3C=CC=CC=3)OC2=O)CC1.Br[C:39]1[CH:44]=[CH:43][C:42]([C@H:45]([CH:64]2[CH2:66][CH2:65]2)[N:46]2[CH2:51][CH2:50][C@:49]([CH2:58][C:59]([OH:62])([CH3:61])[CH3:60])([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[O:48][C:47]2=[O:63])=[CH:41][CH:40]=1.Br[C:68]1[CH:69]=[N:70][C:71]([CH3:74])=[N:72][CH:73]=1>>[CH:64]1([C@@H:45]([C:42]2[CH:43]=[CH:44][C:39]([C:68]3[CH:69]=[N:70][C:71]([CH3:74])=[N:72][CH:73]=3)=[CH:40][CH:41]=2)[N:46]2[CH2:51][CH2:50][C@:49]([CH2:58][C:59]([OH:62])([CH3:61])[CH3:60])([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[O:48][C:47]2=[O:63])[CH2:66][CH2:65]1

Participants

Reactant 3

HCID 143877445-Bromo-2-methylpyrimidine

HCID 49838825HCID 49838825, compound

HCID 68759713HCID 68759713, compound

Product 1

HCID 49838824HCID 49838824, compound

Procedure

The title compound was prepared from 3-{(S)-cyclopropyl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methyl}-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one {prepared in analogy to the intermediate in Example 3 from 3-[(S)-(4-bromo-phenyl)-cyclopropyl-methyl]-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one} and 5-bromo-2-methyl-pyrimidine following a procedure analogous to that described in Example 3. LC-MS (Method 1): tR=3.28 min; Mass spectrum (ESI+): m/z=472 [M+H]+.

Sources & evidence

ORD record: ord-939f5b0a04eb46adba53e41fb70eaaa9
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703765B2

Reaction notes

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