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

HRID 548952

Reaktionsgleichung

Reaktionsgleichung von HRID 548952
[Br:1][C:2]1[C:3]([NH:17][CH:18]2[CH2:20][CH2:19]2)=[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]2[CH2:19][CH2:20]2)=[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

Komponenten

4

Edukt 3

HCID 6342AcetonitrileHCID 517414chloramine-T trihydrateHCID 596831485-Bromo-n4-cyclopropyl-n2-(3-methylsulphanylphenyl)pyrimidine-2,4-diamine

Produkt 1

HCID 131728844(Rs)-s-(3-{[5-bromo-4-(cyclopropylamino)pyrimidin-2-yl]amino}phenyl)-s-methyl-n-(tolylsulphonyl)sulphimide

Versuchsvorschrift

In analogy to Example 1, 0.19 g (0.54 mmol) of 5-bromo-N4-cyclopropyl-N2-(3-methylsulphanylphenyl)pyrimidine-2,4-diamine is reacted with 0.168 g (0.59 mmol) of chloramine-T trihydrate in 5.0 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 0.13 g (47% of theory) of the product.

Aufarbeitung

  1. customPurification by chromatography (silica gel, ethyl acetate/hexane with ethyl acetate 0-100%
  2. customethyl acetate/methanol with methanol 5-10%) results in 0.13 g (47% of theory) of the product

Quellen und Nachweise

ORD-Eintrag
ord-e23aae7b1e8e449498580b57d466bf77
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943629B2

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