Reaktion #87435

ord-f0147134e4364c48bd4999c5edf3e11c

Reaktionsgleichung

[Br][Mg][CH]1CC1
cyclopropylmagnesium bromide
COc1cc(Nc2nc(C=O)cc(COCC(F)(F)F)n2)ccc1-n1cnc(C)c1
2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-4-carbaldehyde
COc1cc(Nc2nc(COCC(F)(F)F)cc(C(O)C3CC3)n2)ccc1-n1cnc(C)c1
title compound
COc1cc(Nc2nc(COCC(F)(F)F)cc(C(O)C3CC3)n2)ccc1-n1cnc(C)c1
Cyclopropyl(2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-yl)methanol

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigewas quenched with ammonium chloride (aq, sat)
  2. 2
    SonstigeThe solvent volume was reduced by evaporation
  3. 3
    ExtraktionThe mixture was extracted with dichloromethane
  4. 4
    Einengenconcentrated in vacuum
  5. 5
    SonstigeThe residue was purified by preparative HPLC

Vorschrift

To an ice-cold solution of cyclopropylmagnesium bromide (1.90 mL, 0.95 mmol) in THF (10 mL), a solution of 2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-4-carbaldehyde (40 mg, 0.09 mmol) in THF (6 mL) was added over 5 min. The mixture was stirred on ice-bath for 30 minutes before it was quenched with ammonium chloride (aq, sat). The solvent volume was reduced by evaporation. The mixture was extracted with dichloromethane, the organic phase was passed through a phase separator and concentrated in vacuum. The residue was purified by preparative HPLC to give the title compound as a dry film, 7 mg (16%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09439904B2uspto-grants-2016_09