2-Methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine → 6-(3-Hydroxy-3-methylazetidin-1-yl)-5-(2-methylpyrimidin-5-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

HRID 923962Notes

Reaction equation

HRID 923962 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:25][C:24]([OH:27])([CH3:26])[CH2:23]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[CH3:28][C:29]1[N:34]=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31][N:30]=1>>[OH:27][C:24]1([CH3:26])[CH2:25][N:22]([C:3]2[C:2]([C:32]3[CH:31]=[N:30][C:29]([CH3:28])=[N:34][CH:33]=3)=[CH:21][C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=3)=[O:8])=[CH:5][N:4]=2)[CH2:23]1

Participants

3

Reactant 2

HCID 457872822-Methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidineHCID 899064985-Bromo-6-(3-hydroxy-3-methylazetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 899078536-(3-Hydroxy-3-methylazetidin-1-yl)-5-(2-methylpyrimidin-5-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 128 using 5-bromo-6-(3-hydroxy-3-methylazetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 128.1) and 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine to afford an off-white solid. HPLC (Condition 4) tR=4.75 min, UPLC-MS (Condition 3) tR=0.95 min, m/z=460.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.29 (s, 3H) 2.68 (s, 3H) 3.58 (s, 4H) 5.47 (s, 1H) 7.26-7.40 (m, 2H) 7.77-7.92 (m, 2H) 8.04 (d, J=2.35 Hz, 1H) 8.67-8.82 (m, 3H) 10.19 (s, 1H).

Workup

  1. customto afford an off-white solid

Sources & evidence

ORD record
ord-26f091752c6e4ce088004fef32b2fc4e
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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