4-Bromo-pyrimidine hydrochloride → 2,6-Dimethyl-4-(pyrimidin-4-yl)aniline

Reaction equation

Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][N:4]=1.[CH3:9][C:10]1[CH:16]=[C:15](B2OC(C)(C)C(C)(C)O2)[CH:14]=[C:13]([CH3:26])[C:11]=1[NH2:12]>>[CH3:9][C:10]1[CH:16]=[C:15]([C:3]2[CH:8]=[CH:7][N:6]=[CH:5][N:4]=2)[CH:14]=[C:13]([CH3:26])[C:11]=1[NH2:12]

Participants

Reactant 2

HCID 213004424-Bromo-pyrimidine hydrochloride

HCID 567377242,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 866972582,6-Dimethyl-4-(pyrimidin-4-yl)aniline

Conditions

Temperature: 70 °C

Procedure

The title compound is prepared from 4-bromopyrimidine hydrochloride and 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline following a procedure analogous to that described in Step 2 of Intermediate 62. The mixture is stirred for 12 hours at 70° C. LC (method 9): tR=0.74 min; Mass spectrum (ESI+): m/z=200 [M+H]+.