4-Chloro-2-methoxypyrimidine → 4-(2-Methoxypyrimidin-4-yl)-2,6-dimethylaniline

HRID 237598Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[N:3]=1.[CH3:10][C:11]1[CH:17]=[C:16](B2OC(C)(C)C(C)(C)O2)[CH:15]=[C:14]([CH3:27])[C:12]=1[NH2:13]>>[CH3:9][O:8][C:4]1[N:3]=[C:2]([C:16]2[CH:15]=[C:14]([CH3:27])[C:12]([NH2:13])=[C:11]([CH3:10])[CH:17]=2)[CH:7]=[CH:6][N:5]=1

Participants

Reactant 2

HCID 5752304-Chloro-2-methoxypyrimidine

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

Product 1

HCID 866972644-(2-Methoxypyrimidin-4-yl)-2,6-dimethylaniline

Conditions

Temperature: 60 °C

Procedure

The title compound is prepared from 4-chloro-2-methoxypyrimidine 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 60° C. LC (method 14): tR=0.89 min; Mass spectrum (ESI+): m/z=230 [M+H]+.

Sources & evidence

ORD record: ord-af1cfec148d342fd8921d7d62c16b150
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642585B2

Reaction notes

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