Ethanol → 1-(2-(3-Methoxy-4-(4-methoxy-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)-methyl)pyrimidin-4-yl)ethanol

HRID 59159Notes

Reaction equation

HRID 59159 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:16][C:17]2[N:22]=[C:21]([C:23](=[O:25])[CH3:24])[CH:20]=[C:19]([CH2:26][O:27][CH2:28][C:29]([F:32])([F:31])[F:30])[N:18]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([O:14][CH3:15])[N:11]=[CH:10]1.C(O)C>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:16][C:17]2[N:22]=[C:21]([CH:23]([OH:25])[CH3:24])[CH:20]=[C:19]([CH2:26][O:27][CH2:28][C:29]([F:30])([F:31])[F:32])[N:18]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([O:14][CH3:15])[N:11]=[CH:10]1

Participants

4

Reactant 2

HCID 702EthanolHCID 117823955HCID 117823955, compound

Product 1

HCID 863444361-(2-(3-Methoxy-4-(4-methoxy-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)-methyl)pyrimidin-4-yl)ethanol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 1-(2-(3-methoxy-4-(4-methoxy-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-yl)ethanone (0.1 g, 0.22 mmol) in ethanol (5 mL) sodium borohydride (0.034 g, 0.89 mmol) was added. The mixture was stirred at rt for 10 min. Acetone (2 mL) was added and mixture was stirred for 20 min. The mixture was filtered, the filtrate was concentrated in vacuum and the residue was purified by preparative HPLC to give the title compound as a dry film, 50 mg (50%).

Workup

  1. stirringmixture was stirred for 20 min
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuum
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-1bc7ba78bbfe4519aa1f782903ca4504
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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