Methanol → 6-(4-(1-(2-(Dimethylamino)ethyl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-5-ethylpyrimidin-4-amine

HRID 2284007Notes

Reaction equation

HRID 2284007 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]([CH3:43])[CH2:10][CH2:11][N:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([C:24]([F:27])([F:26])[F:25])[CH:18]=2)[N:14]=[C:13]1[CH:28]1[CH2:33][CH2:32][N:31]([C:34]2[N:39]=[CH:38][N:37]=[C:36]([NH2:40])[C:35]=2[CH:41]=[CH2:42])[CH2:30][CH2:29]1.CO>[Pd]>[CH3:8][N:9]([CH3:43])[CH2:10][CH2:11][N:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([C:24]([F:27])([F:25])[F:26])[CH:18]=2)[N:14]=[C:13]1[CH:28]1[CH2:29][CH2:30][N:31]([C:34]2[N:39]=[CH:38][N:37]=[C:36]([NH2:40])[C:35]=2[CH2:41][CH3:42])[CH2:32][CH2:33]1

Participants

4

Reactant 2

HCID 887MethanolHCID 1317335316-[4-[1-[2-(Dimethylamino)ethyl]-4-[4-fluoro-3-(trifluoromethyl)phenyl]imidazol-2-yl]piperidin-1-yl]-5-ethenylpyrimidin-4-amine;2,2,2-trifluoroacetic acid

Product 1

HCID 894424656-(4-(1-(2-(Dimethylamino)ethyl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-5-ethylpyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a 10 mL round-bottom flask containing 6-{4-[1-(2-dimethylamino-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-5-vinyl-pyrimidin-4-ylamine; compound with trifluoro-acetic acid (25.00 mg; 0.04 mmol; 1.00 eq.) in methanol (2.00 ml; 49.37 mmol; 1231.95 eq.) under argon was slowly poured 10% Pd/C (80.00 mg; 0.75 mmol; 18.76 eq.). The round-bottom flask was vacuumed and then filled with H2. The procedure was repeated for 4 more times before the mixture was stirred at rt for O/N under H2 (balloon). The obtained mixture was filtered and then purified with Waters pre-HPLC. LC-MS: (M+1=506, obsd.=506).

Workup

  1. additionfilled with H2
  2. filtrationThe obtained mixture was filtered
  3. custompurified with Waters pre-HPLC

Sources & evidence

ORD record
ord-765631dae9c84bfba5970c8ece4253da
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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