m-Chloroperbenzoic acid → HCID 18778875, compound

HRID 2396031Notes

Reaction equation

HRID 2396031 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3[CH:16]=[N:17][CH:18]=[N:19][CH:20]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:26]>ClCCl>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3[CH:16]=[N:17][CH:18]=[N+:19]([O-:26])[CH:20]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18778867HCID 18778867, compound

Product 1

HCID 18778875HCID 18778875, compoundYield 26,876.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(3-Cyclopentyloxy-4-methoxyphenyl)pyrimidine (1.37 g) and 3-chloroperoxybenzoic acid (50.60%) (1.75 g) in dichloromethane (35 ml) was stirred at RT and the reaction followed by t.l.c. After 5 days, the reaction mixture was partitioned three times between dichloromethane (50 ml) and 10% aqueous Na2SO3 solution (50 ml). The combined organic phase was washed with 5% aqueous NaOH solution (3×30 ml), brine (30 ml), dried (MgSO4) and evaporated to afford a tan solid. Flash chromatography [SiO2 ; dichloromethane/EtOAc, 1:9 then dichloromethane/EtOAc/methane, 1:8:1] followed by recrystallisation from EtOAc furnished the title compound (390 g) as a white powder (mp 140°-143° C.). Found=C, 67.03; H, 6.31; N, 9.81. C16H18N2O3 requires C, 67.12; H, 6.34; N, 9.78%.

Workup

  1. customthe reaction mixture was partitioned three times between dichloromethane (50 ml) and 10% aqueous Na2SO3 solution (50 ml)
  2. washThe combined organic phase was washed with 5% aqueous NaOH solution (3×30 ml), brine (30 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto afford a tan solid
  6. customdichloromethane/EtOAc, 1:9 then dichloromethane/EtOAc/methane, 1:8:1] followed by recrystallisation from EtOAc

Sources & evidence

ORD record
ord-d0ccc411c4ab4f6c8a0392ce6304ab0c
Source dataset
uspto-grants-1996_02
Patent number
US05491147

Reaction notes

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