(4,6-dichloropyrimidin-5-yl)[1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]methanone → (4,6-dichloropyrimidin-5-yl)[1-(4-ethylphenyl)-1H-imidazol-5-yl]methanone
Reaction equation
[Cl:1][C:2]1[C:7]([CH:8]([C:10]2[N:14]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][CH:16]=3)[CH:13]=[N:12][CH:11]=2)[OH:9])=[C:6]([Cl:23])[N:5]=[CH:4][N:3]=1.ClC1C(C(C2C=NN(C)C=2C2C=CC(C)=CC=2)=O)=C(Cl)N=CN=1>C(OCC)(=O)C>[Cl:23][C:6]1[C:7]([C:8]([C:10]2[N:14]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][CH:16]=3)[CH:13]=[N:12][CH:11]=2)=[O:9])=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
(4,6-Dichloropyrimidin-5-yl)[1-(4-ethylphenyl)-1H-imidazol-5-yl]methanol (C20) was converted to the product using a procedure analogous to that described for the synthesis of (4,6-dichloropyrimidin-5-yl)[1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]methanone (C5) in Example 1, step 5, except that the ethyl acetate layer was washed with aqueous sodium bicarbonate solution rather than aqueous sodium hydroxide solution. Recrystallization was not carried out in this case; the product was obtained as a solid. Yield: 701 mg, 2.02 mmol, 94%. LCMS m/z 346.9 (M+1). 1H NMR (500 MHz, CDCl3) δ 1.31 (t, J=7.6 Hz, 3H), 2.75 (q, J=7.6 Hz, 2H), 7.30-7.36 (m, 4H), 7.61 (br s, 1H), 7.85 (d, J=0.8 Hz, 1H), 8.85 (s, 1H).