2-Chloro-5-fluoropyrimidine → HCID 58485370, compound

HRID 1046077Notes

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

Participants

Reactant 2

HCID 5834662-Chloro-5-fluoropyrimidine

HCID 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 58485370HCID 58485370, 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 2-chloro-5-fluoropyrimidine a procedure analogous to that described in Example 1 Step 2. LC-MS Method 2 tR=1.327 min, m/z=391.9; 1H NMR (CDCl3) 1.11 (s, 3H), 1.18 (s, 3H), 1.52 (d, 3H), 2.20 (m, 4H), 2.38 (m, 1H), 2.85 (m, 1H), 5.72 (m, 1H), 7.08 (m, 2H), 7.20-7.40 (m, 5H), 8.12 (m, 2H), 8.61 (m, 2H)

Sources & evidence

ORD record: ord-436acd9b9cf144498558ae9f5c7f951d
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569292B2

Reaction notes

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