1,3-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydropyridin-2-one → US10023592, Example 144

HRID 518355Notes

Reaction equation

HRID 518355 reaction equation
Cl[C:2]1[C:7]([O:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[CH:6][N:5]=[C:4]([CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[N:3]=1.[CH3:18][N:19]1[CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=[C:21]([CH3:34])[C:20]1=[O:35]>>[CH:10]1([CH2:9][O:8][C:7]2[C:2]([C:23]3[CH:22]=[C:21]([CH3:34])[C:20](=[O:35])[N:19]([CH3:18])[CH:24]=3)=[N:3][C:4]([CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])=[N:5][CH:6]=2)[CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 712703091,3-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydropyridin-2-oneHCID 1180221364-Chloro-5-(cyclopropylmethoxy)-2-(methylsulfonylmethyl)pyrimidine

Product 1

HCID 118021646US10023592, Example 144

Procedure

The title compound of Example 143, step 2 was reacted with 1,3-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one in a manner similar to Example 143, step 3 to give the title compound. 1H NMR (CDCl3, 400 MHz) δ 8.49 (d, J=2.0 Hz, 1H), 8.18 (s, 1H), 7.60 (s, 1H), 3.86 (d, J=6.8 Hz, 2H), 3.67 (s, 3H), 3.11 (s, 3H), 2.24 (s, 3H), 1.29-1.27 (m, 1H), 0.72-0.67 (m, 2H), 0.39-0.35 (m, 2H). LCMS: 364.1 (M+1)+

Sources & evidence

ORD record
ord-6902869b2c154c2090346fc4fca24a46
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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