(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

HRID 72718Notes

Reaction equation

HRID 72718 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]=1

Participants

4

Reactant 2

HCID 86712558(4,6-dichloropyrimidin-5-yl)[1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]methanoneHCID 86712566(4,6-dichloropyrimidin-5-yl)[1-(4-ethylphenyl)-1H-imidazol-5-yl]methanol

Product 1

HCID 86712567(4,6-dichloropyrimidin-5-yl)[1-(4-ethylphenyl)-1H-imidazol-5-yl]methanone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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).

Workup

  1. washwas washed with aqueous sodium bicarbonate solution rather than aqueous sodium hydroxide solution
  2. customRecrystallization
  3. customthe product was obtained as a solid

Sources & evidence

ORD record
ord-ab81641de13a4f29b9ddae65fab4c105
Source dataset
uspto-grants-2014_09
Patent number
US08829010B2

Reaction notes

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