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5-bromo-1-methylpyrimidin-2(1H)-one → 5-bromo-1-methylpyrimidin-2(1H)-one

HRID 2045996
Notes
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Reaction equation

HRID 2045996 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:36][C:37]1[CH:38]=[N:39][C:40](=[O:44])[N:41]([CH3:43])[CH:42]=1.BrC1C=NC(O)=NC=1>>[OH:1][C:2]([CH3:34])([CH3:35])[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:37]3[CH:38]=[N:39][C:40](=[O:44])[N:41]([CH3:43])[CH:42]=3)=[CH:17][CH:18]=2)[CH3:12])[CH2:6][CH2:5]1.[Br:36][C:37]1[CH:38]=[N:39][C:40](=[O:44])[N:41]([CH3:43])[CH:42]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1397075-bromo-1-methylpyrimidin-2(1H)-oneHCID 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-oneHCID 178517598HCID 178517598, compound

Product 2

HCID 1397075-bromo-1-methylpyrimidin-2(1H)-one
HCID 44512036
(S)-6-(2-hydroxy-2-methylpropyl)-3-((S)-1-(4-(1-methyl-2-oxo-1,2-dihydropyrimidin-5-yl)phenyl)ethyl)-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-1-methylpyrimidin-2(1H)-one following a procedure analogous to that described in Example 1 Step 3. 5-bromo-1-methylpyrimidin-2(1H)-one was prepared from 5-bromopyrimidin-2-ol following a procedure analogous to that described in Example 1 Step 2. LC-MS Method 2 tR=1.068 min, m/z=462.1; 1H NMR (CD3OD) 0.95 (s, 3H), 1.28 (m, 3H), 1.54 (m, 3H), 2.15 (d, 2H), 2.20 (m, 1H), 2.47 (m, 2H), 3.04 (m, 1H), 3.63 (s, 2H), 5.56 (m, 1H), 7.06 (m, 2H), 7.29-7.37 (m, 7H), 8.40 (d, 1H), 8.81 (d, 1H)

Sources & evidence

ORD record
ord-299dc8693850489e9cfaa2857fe66aa2
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08592410B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes