5-bromo-1-methyl-1H-pyrazole-4-carbaldehyde → (5-bromo-1-methyl-1H-pyrazol-4-yl)(4,6-dichloropyrimidin-5-yl)methanol

HRID 72723Notes

Reaction equation

HRID 72723 reaction equation
[Br:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[CH:8]=[O:9].[Cl:10][C:11]1[C:16](C(C2C=NN(C)C=2C2C=CC(C)=CC=2)O)=[C:15]([Cl:32])[N:14]=[CH:13][N:12]=1>>[Br:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[CH:8]([C:16]1[C:11]([Cl:10])=[N:12][CH:13]=[N:14][C:15]=1[Cl:32])[OH:9]

Participants

3

Reactant 2

HCID 547753935-bromo-1-methyl-1H-pyrazole-4-carbaldehydeHCID 86712557(4,6-dichloropyrimidin-5-yl)[1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]methanol

Product 1

HCID 86712569(5-bromo-1-methyl-1H-pyrazol-4-yl)(4,6-dichloropyrimidin-5-yl)methanol

Procedure

5-Bromo-1-methyl-1H-pyrazole-4-carbaldehyde (C24) 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. In this case the product was purified not by recrystallization, but using silica gel chromatography (Eluent: 10:1 heptane/ethyl acetate, then 2:1 heptane/ethyl acetate). Yield: 1.26 g, 3.73 mmol, 70%. LCMS m/z 339.1 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.4-3.0 (v br s, 1H), 3.88 (s, 3H), 6.36 (s, 1H), 7.56 (s, 1H), 8.74 (s, 1H).

Workup

  1. customIn this case the product was purified not by recrystallization

Sources & evidence

ORD record
ord-5d3add6f2f2e4b0984cb4a9d60e24c02
Source dataset
uspto-grants-2014_09
Patent number
US08829010B2

Reaction notes

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