4-Chloro-5-(cyclopropylmethoxy)-2-(methylsulfonylmethyl)pyrimidine → US10023592, Example 145

HRID 575626Notes

Reaction equation

HRID 575626 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:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:38]3[CH:39]=[N:40][N:41]([CH3:43])[CH:42]=3)[CH:25]=2)[C:20]1=[O:44]>>[CH:10]1([CH2:9][O:8][C:7]2[C:2]([C:27]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:38]5[CH:39]=[N:40][N:41]([CH3:43])[CH:42]=5)[CH:25]=4)[C:20](=[O:44])[N:19]([CH3:18])[CH:28]=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 1180221364-Chloro-5-(cyclopropylmethoxy)-2-(methylsulfonylmethyl)pyrimidineHCID 1237513492-Methyl-6-(1-methylpyrazol-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1-one

Product 1

HCID 118021425US10023592, Example 145

Procedure

The title compound of Example 143, step 2 was reacted with the title compound of Example 46, step 2 in a manner similar to Example 143, step 3 to give the title compound. 1H NMR (DMSO-d6, 400 MHz) δ 8.26 (d, J=8.4 Hz, 1H), 8.23 (s, 1H), 7.91 (s, 1H), 7.5 (d, J=8.4 Hz, 1H), 7.70 (s, 1H), 7.66 (s, 1H), 7.52 (s, 1H), 3.87 (s, 3H), 3.85-3.80 (m, 4H), 3.57 (s, 3H), 3.28 (s, 3H), 0.88-0.87 (m, 1H), 0.30-0.25 (m, 2H), 0.07-0.04 (m, 2H). LCMS: 480.2 (M+1)+

Sources & evidence

ORD record
ord-7272efd527e04108ba419057ce326af9
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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