Water → 4-amino-6-(4-{4-[4-fluoro-3-(trifluoromethyl)phenyl]-1-methyl-1H-imidazol-2-yl}piperidin-1-yl)pyrimidine-5-carbaldehyde

HRID 2283955Notes

Reaction equation

HRID 2283955 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[N:11]([CH3:13])[CH:12]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].[NH2:24][C:25]1[C:30]([CH:31]=[O:32])=[C:29](Cl)[N:28]=[CH:27][N:26]=1.CCN(C(C)C)C(C)C.O>C(#N)C>[NH2:24][C:25]1[C:30]([CH:31]=[O:32])=[C:29]([N:17]2[CH2:18][CH2:19][CH:14]([C:10]3[N:11]([CH3:13])[CH:12]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:20]([F:21])([F:22])[F:23])[CH:4]=4)[N:9]=3)[CH2:15][CH2:16]2)[N:28]=[CH:27][N:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 842305-Pyrimidinecarboxaldehyde, 4-amino-6-chloro-HCID 866320214-(4-(4-Fluoro-3-(trifluoromethyl)phenyl)-1-methyl-1H-imidazol-2-yl)piperidine

Product 1

HCID 894427184-amino-6-(4-{4-[4-fluoro-3-(trifluoromethyl)phenyl]-1-methyl-1H-imidazol-2-yl}piperidin-1-yl)pyrimidine-5-carbaldehydeYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-methyl-1h-imidazol-2-yl]-piperidine (600.00 mg; 1.83 mmol; 1.0 eq.), 4-amino-6-chloropyrimidine-5-carbaldehyde (303.25 mg; 1.92 mmol; 1.05 eq.), DIEA (0.95 ml; 5.5 mmol; 3.0 eq.) in acetonitrile (10.0 ml) was heated at 40° C. for 1 h. The reaction mixture was poured into water. The precipitate was filtered, washed with water and dried under vacuum to afford the title compound in 85% yield. LC-MS: (M+1=449, obsd.=449).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-90d5872d6c1d408d916f3f94226c913b
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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