Isopropanol → 5-Bromo-2-[(phenylmethyl)sulfinyl]pyrimidine

HRID 905237Notes

Reaction equation

HRID 905237 reaction equation
[CH2:1]([S:8][C:9]1[N:14]=[CH:13][C:12]([Br:15])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:24])C=1.CC(O)C>ClCCl>[CH2:1]([S:8]([C:9]1[N:10]=[CH:11][C:12]([Br:15])=[CH:13][N:14]=1)=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 70297m-Chloroperbenzoic acidHCID 204757122-(Benzylsulfanyl)-5-bromopyrimidine

Product 1

HCID 204757185-Bromo-2-[(phenylmethyl)sulfinyl]pyrimidineYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The oxidation of 2-benzylthio-5-bromopyrimidine was carried out using one molar equivalent of 85% m-chloroperbenzoic acid in dichloromethane, initially at -10° C. and then at 0° C., as described in Example 40 above; yield 91%, m.p. 101° C. (iPrOH). 1H NMR (CDCl3); δ4.26 and 4.31 (CH2), 7.16 (Ph), 8.80 (H-4, H-6).

Workup

  1. custominitially at -10° C.
  2. customat 0° C.

Sources & evidence

ORD record
ord-494365b70ba743d1b0ac86136f4fdd02
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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