4-Chloro-5-(2,4-difluorophenoxy)-2-(methylsulfonylmethyl)pyrimidine → US10023592, Example 148

HRID 575628Notes

Reaction equation

HRID 575628 reaction equation
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])=[CH:6][N:5]=[C:4]([CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])[N:3]=1.[CH3:22][N:23]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]1=[O:42]>>[F:16][C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[O:8][C:7]1[C:2]([C:31]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24](=[O:42])[N:23]([CH3:22])[CH:32]=2)=[N:3][C:4]([CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])=[N:5][CH:6]=1

Participants

3

Reactant 2

HCID 1180223714-Chloro-5-(2,4-difluorophenoxy)-2-(methylsulfonylmethyl)pyrimidineHCID 1238094992-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1(2H)-one

Product 1

HCID 118021882US10023592, Example 148

Procedure

The title compound of Example 146, step 2 was reacted with the title compound of Example 89, step 1 in a manner similar to Example 143, step 3 to give the title compound. 1H NMR (DMSO-d6, 400 MHz) δ 8.62 (s, 1H), 8.28 (d, J=8.0 Hz, 1H), 7.91 (s, 1H), 7.69-7.68 (m, 2H), 7.58-7.54 (m, 1H), 7.45-7.34 (m, 2H), 7.07-7.03 (m, 1H), 4.83 (s, 2H), 3.58 (s, 3H), 3.17 (s, 3H). LCMS: 458.1 (M+1)+

Sources & evidence

ORD record
ord-27157b1672d84669b7bc2e5e70fd57b6
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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