m-Chloroperbenzoic acid → 5-Bromo-2-[(thiophen-2-yl)methanesulfinyl]pyrimidine

HRID 905232Notes

Reaction equation

HRID 905232 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH2:17][S:18][C:19]1[N:24]=[CH:23][C:22]([Br:25])=[CH:21][N:20]=1>ClCCl>[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH2:17][S:18]([C:19]1[N:24]=[CH:23][C:22]([Br:25])=[CH:21][N:20]=1)=[O:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 20475699HCID 20475699, compound

Product 1

HCID 1332585-Bromo-2-[(thiophen-2-yl)methanesulfinyl]pyrimidineYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

85% m-Chloroperbenzoic acid (1.5 mmol) was added to a solution of 2-(2-thienylmethylthio)-5-bromopyrimidine (1.5 mmol) in dichloromethane (25 ml) at -10° C. and the solution left at 0° C. for 18 h. The dichloromethane solution was then washed with saturated aqueous solutions of Na2SO and NaHCO3, and the dried (MgSO4) solution evaporated to leave the title compound; yield 53%, m.p. 108°-109° C. (iPrOH). 1H NMR (CDCl3) δ4.53 (CH2, 6.9 (H-3', H-4'), 7.16 (H-5'), 8.83 (H-4, H-6).

Workup

  1. washThe dichloromethane solution was then washed with saturated aqueous solutions of Na2SO and NaHCO3
  2. dry with materialthe dried (MgSO4) solution
  3. customevaporated

Sources & evidence

ORD record
ord-8ca5d55e1db345b4930439a0518b6115
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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