5-Bromo-2-methylpyrimidine → HCID 58485381, compound

HRID 1046082Notes

Reaction equation

[CH3:1][C:2]1[O:6][C:5]([CH2:7][CH2:8][C@@:9]2([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[O:14][C:13](=[O:15])[N:12]([C@H:16]([C:18]3[CH:23]=[CH:22][C:21](B4OC(C)(C)C(C)(C)O4)=[CH:20][CH:19]=3)[CH3:17])[CH2:11][CH2:10]2)=[N:4][N:3]=1.Br[C:40]1[CH:41]=[N:42][C:43]([CH3:46])=[N:44][CH:45]=1>>[CH3:1][C:2]1[O:6][C:5]([CH2:7][CH2:8][C@@:9]2([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[O:14][C:13](=[O:15])[N:12]([C@H:16]([C:18]3[CH:19]=[CH:20][C:21]([C:40]4[CH:41]=[N:42][C:43]([CH3:46])=[N:44][CH:45]=4)=[CH:22][CH:23]=3)[CH3:17])[CH2:11][CH2:10]2)=[N:4][N:3]=1

Participants

Reactant 2

HCID 143877445-Bromo-2-methylpyrimidine

HCID 59635664HCID 59635664, compound

Product 1

HCID 58485381HCID 58485381, compound

Procedure

The title compound was prepared from (R)-6-(2-(5-methyl-1,3,4-oxadiazol-2-yl)ethyl)-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-methylpyrimidine following a procedure analogous to that described in Example 1 Step 2. LC-MS Method 2 tR=1.035 min, m/z=484.1; 1H NMR (CD3OD) 1.57 (m, 3H), 2.29 (m, 2H), 2.38 (m, 1H), 2.41 (s, 3H), 2.47 (m, 1H), 2.50 (m, 1H), 2.63 (m, 1H), 2.72 (s, 3H), 2.96 (m, 1H), 3.15 (m, 1H), 5.58 (m, 1H), 7.12 (m, 2H), 7.33 (m, 3H), 7.38 (m, 2H), 7.47 (m, 2H), 8.88 (s, 2H).

Sources & evidence

ORD record: ord-e7733aa72cdd48e89d031cf41fbee045
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569292B2

Reaction notes

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