(4,6-dichloropyrimidin-5-yl)[1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]methanol → (4,6-dichloropyrimidin-5-yl)[1-(4-ethylphenyl)-1H-imidazol-5-yl]methanol

HRID 72717Notes

Reaction equation

HRID 72717 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH:14]=[O:15])=[CH:12][N:11]=[CH:10]2)=[CH:5][CH:4]=1)[CH3:2].[Cl:16][C:17]1[C:22](C(C2C=NN(C)C=2C2C=CC(C)=CC=2)O)=[C:21]([Cl:38])[N:20]=[CH:19][N:18]=1>>[Cl:16][C:17]1[C:22]([CH:14]([C:13]2[N:9]([C:6]3[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][CH:7]=3)[CH:10]=[N:11][CH:12]=2)[OH:15])=[C:21]([Cl:38])[N:20]=[CH:19][N:18]=1

Participants

3

Reactant 2

HCID 86712557(4,6-dichloropyrimidin-5-yl)[1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]methanolHCID 867125651-(4-ethylphenyl)-1H-imidazole-5-carbaldehyde

Product 1

HCID 86712566(4,6-dichloropyrimidin-5-yl)[1-(4-ethylphenyl)-1H-imidazol-5-yl]methanol

Procedure

1-(4-Ethylphenyl)-1H-imidazole-5-carbaldehyde (C19) 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]methanol (C4) in Example 1, step 4. The crude product, a yellow solid, was washed with a 1:1 mixture of heptane and ethyl acetate to afford the product. Yield: 473 mg, 1.35 mmol, 74%. LCMS m/z 348.9 (M+1). 1H NMR (500 MHz, CDCl3) δ 1.29 (t, J=7.6 Hz, 3H), 2.73 (q, J=7.6 Hz, 2H), 6.27 (br s, 1H), 7.14-7.15 (m, 1H), 7.28-7.33 (m, 4H), 7.69 (d, J=0.7 Hz, 1H), 8.68 (s, 1H).

Workup

  1. washThe crude product, a yellow solid, was washed with a 1:1 mixture of heptane and ethyl acetate
  2. customto afford the product

Sources & evidence

ORD record
ord-3e11df17725b4e38af2e7b6b1539e6f0
Source dataset
uspto-grants-2014_09
Patent number
US08829010B2

Reaction notes

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