m-Chloroperbenzoic acid → 5-bromo-N4-isopropyl-N2-[4-(methylsulfinyl)phenyl)-pyrimidine-2,4-diamine

HRID 1891065Notes

Reaction equation

HRID 1891065 reaction equation
Cl.[Br:2][C:3]1[C:4]([NH:18][CH:19]([CH3:21])[CH3:20])=[N:5][C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=2)=[N:7][CH:8]=1.ClC1C=C(C=CC=1)C(OO)=[O:27]>C(Cl)Cl>[Br:2][C:3]1[C:4]([NH:18][CH:19]([CH3:21])[CH3:20])=[N:5][C:6]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([S:16]([CH3:17])=[O:27])=[CH:14][CH:15]=2)=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 687016295-bromo-N4-isopropyl-N2-[4-(methylsulfanyl)phenyl)-pyrimidine-2,4-diamine hydrochloride

Product 1

HCID 596740175-bromo-N4-isopropyl-N2-[4-(methylsulfinyl)phenyl)-pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.77 g (4.6 mmol) of 5-bromo-N4-isopropyl-N2-[4-(methylsulfanyl)phenyl)-pyrimidine-2,4-diamine hydrochloride is taken up in 40 ml of DCM and mixed with 1.73 g (5.5 mmol) of 3-chloroperoxybenzoic acid (55%). The batch is stirred for 90 minutes at room temperature and then diluted with DCM. It is washed with saturated NaHCO3 solution and saturated NaCl solution. The organic phase is dried (Na2SO4), filtered and concentrated by evaporation. The remaining residue is purified by chromatography (DCM/EtOH 9:1). 553 mg (1.5 mmol, corresponding to 33% of theory) of the product is obtained.

Workup

  1. washIt is washed with saturated NaHCO3 solution and saturated NaCl solution
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe remaining residue is purified by chromatography (DCM/EtOH 9:1)
  6. custom553 mg (1.5 mmol, corresponding to 33% of theory) of the product is obtained

Sources & evidence

ORD record
ord-e1e6279c394a4c849c693e7672de4e1c
Source dataset
uspto-grants-2013_08
Patent number
US08507510B2

Reaction notes

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