[2-(Dimethylamino)pyrimidin-5-yl]boronic acid → 6'-{4-[4-(4-Fluoro-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-N2,N2-dimethyl-[5,5']bipyrimidinyl-2,4'-diamine

HRID 2283976Notes

Reaction equation

HRID 2283976 reaction equation
FC1C=[CH:6][C:5]([C:8]2[C:9]([NH2:37])=[N:10][CH:11]=[N:12][C:13]=2[N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[N:21]([CH3:36])[CH:22]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[C:27]([C:32]([F:35])([F:34])[F:33])[CH:26]=4)[N:24]=3)[CH2:16][CH2:15]2)=[CH:4]C=1.[CH3:38][N:39]([CH3:49])[C:40]1[N:45]=CC(B(O)O)=C[N:41]=1>>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:23]2[N:24]=[C:20]([CH:17]3[CH2:18][CH2:19][N:14]([C:13]4[N:12]=[CH:11][N:10]=[C:9]([NH2:37])[C:8]=4[C:5]4[CH:4]=[N:41][C:40]([N:39]([CH3:49])[CH3:38])=[N:45][CH:6]=4)[CH2:15][CH2:16]3)[N:21]([CH3:36])[CH:22]=2)=[CH:26][C:27]=1[C:32]([F:35])([F:33])[F:34]

Participants

3

Reactant 2

HCID 45088929[2-(Dimethylamino)pyrimidin-5-yl]boronic acidHCID 894424825-(4-Fluoro-phenyl)-6-{4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidin-4-ylamine

Product 1

HCID 894506186'-{4-[4-(4-Fluoro-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-N2,N2-dimethyl-[5,5']bipyrimidinyl-2,4'-diamine

Procedure

The title compound was prepared in an analogous manner as 5-(4-Fluoro-phenyl)-6-{4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidin-4-ylamine using (2-(dimethylamino)pyrimidin-5-yl)boronic acid instead of 4-fluorophenylboronic acid. LC-MS: (M+1=542, obsd.=542).

Sources & evidence

ORD record
ord-06274ede86034736b310a6c84c15908b
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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