Acetonitrile → (Rs)-s-(3-{[5-bromo-4-(isopropylamino)pyrimidin-2-yl]amino}phenyl)-s-methyl-n-(tolylsulphonyl)sulphimide

HRID 548949

Reaction equation

HRID 548949 reaction equation
[Br:1][C:2]1[C:3]([NH:17][CH:18]([CH3:20])[CH3:19])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([S:15][CH3:16])[CH:10]=2)=[N:6][CH:7]=1.C[C:22]1[CH:27]=[CH:26][C:25]([S:28]([N-:31]Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.O.O.O.[Na+].[C:37](#N)C>>[Br:1][C:2]1[C:3]([NH:17][CH:18]([CH3:20])[CH3:19])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[C:11]([S:15]([CH3:16])=[N:31][S:28]([C:25]3[CH:24]=[CH:23][CH:22]=[CH:27][C:26]=3[CH3:37])(=[O:29])=[O:30])[CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 517414chloramine-T trihydrateHCID 596831645-Bromo-n4-isopropyl-n2-(3-methylsulphanylphenyl)pyrimidine-2,4-diamine

Product 1

HCID 131728843(Rs)-s-(3-{[5-bromo-4-(isopropylamino)pyrimidin-2-yl]amino}phenyl)-s-methyl-n-(tolylsulphonyl)sulphimide

Procedure

In analogy to Example 1, 0.15 g (0.42 mmol) of 5-bromo-N4-isopropyl-N2-(3-methylsulphanylphenyl)pyrimidine-2,4-diamine is reacted with 0.132 g (0.47 mmol) of chloramine-T trihydrate in 3.0 ml of acetonitrile (24 hours). Purification by chromatography (silica gel, ethyl acetate/hexane with ethyl acetate 0-100%, then ethyl acetate/methanol with methanol 5-10% results in 0.14 g (63% of theory) of the product.

Workup

  1. customPurification by chromatography (silica gel, ethyl acetate/hexane with ethyl acetate 0-100%
  2. customethyl acetate/methanol with methanol 5-10% results in 0.14 g (63% of theory) of the product

Sources & evidence

ORD record
ord-5f8d6b45db184f5ca026f8130a4e25a7
Source dataset
uspto-grants-2011_05
Patent number
US07943629B2

Linked notes

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