m-Chloroperbenzoic acid → 4-(4,6-Dimethyl-1-oxidopyrimidin-5-yl)-3-methylphenol

HRID 69327Notes

Reaction equation

HRID 69327 reaction equation
[CH3:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=2[CH3:15])=[C:6]([CH3:16])[N:5]=[CH:4][N:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:22]>ClCCl>[CH3:16][C:6]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=2[CH3:15])=[C:2]([CH3:1])[N+:3]([O-:22])=[CH:4][N:5]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 867178264-(4,6-Dimethylpyrimidin-5-yl)-3-methylphenol

Product 1

HCID 867178254-(4,6-Dimethyl-1-oxidopyrimidin-5-yl)-3-methylphenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(4,6-dimethylpyrimidin-5-yl)-3-methylphenol (1.0 g, 4.7 mmol) in dichloromethane (25 mL) was added 3-chloroperoxybenzoic acid (887 mg, 5.14 mmol) at 0° C. The reaction was stirred at 0° C. for 2 hours, then at room temperature for 14 hours. After removal of solvent in vacuo, purification by chromatography on silica gel (Gradient: 0% to 100% ethyl acetate in petroleum ether) provided the product. Yield: 742 mg, 3.22 mmol, 69%. 1H NMR (400 MHz, CDCl3) δ 9.03 (s, 1H), 6.82-6.91 (m, 3H), 2.30 (s, 3H), 2.22 (s, 3H), 1.97 (s, 3H).

Workup

  1. waitat room temperature for 14 hours
  2. customAfter removal of solvent
  3. customin vacuo, purification by chromatography on silica gel (Gradient: 0% to 100% ethyl acetate in petroleum ether)
  4. customprovided the product

Sources & evidence

ORD record
ord-4203d0a5b4ae41c7bdac807455240a5f
Source dataset
uspto-grants-2014_09
Patent number
US08822494B2

Reaction notes

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