Sodium borohydride → 5-[5-Bromo-4-(1-ethyl-2-hydroxy-propylsulfanyl)-pyrimidin-2-ylamino]-pyridine-2-sulfonic acid amide

HRID 1182062

Reaction equation

HRID 1182062 reaction equation
[Br:1][C:2]1[C:3]([S:19][CH:20]([CH2:24][CH3:25])[C:21](=[O:23])[CH3:22])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([S:15]([NH2:18])(=[O:17])=[O:16])=[N:13][CH:14]=2)=[N:6][CH:7]=1.[BH4-].[Na+]>C1COCC1.CO.C(O)(=O)C>[Br:1][C:2]1[C:3]([S:19][CH:20]([CH2:24][CH3:25])[CH:21]([OH:23])[CH3:22])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([S:15]([NH2:18])(=[O:17])=[O:16])=[N:13][CH:14]=2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 589818355-[5-Bromo-4-(1-ethyl-2-oxo-propylsulfanyl)-pyrimidin-2-ylamino]-pyridine-2-sulfonic acid amide

Product 1

HCID 589818875-[5-Bromo-4-(1-ethyl-2-hydroxy-propylsulfanyl)-pyrimidin-2-ylamino]-pyridine-2-sulfonic acid amide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

26 mg (0.058 mmol) of 5-[5-bromo-4-(1-ethyl-2-oxo-propylsulfanyl)-pyrimidin-2-ylamino]-pyridine-2-sulfonic acid amide, dissolved in 1.5 ml of THF/MeOH 1:1, is mixed with 10 mg of sodium borohydride and stirred for 3 hours at room temperature. While being cooled, 2-3 drops of glacial acetic acid are added and concentrated by evaporation. Uptake in acetonitrile and suctioning-off yield 17 mg (65% of theory) of 5-[5-bromo-4-(1-ethyl-2-hydroxy-propylsulfanyl)-pyrimidin-2-ylamino]-pyridine-2-sulfonic acid amide.

Workup

  1. temperatureWhile being cooled
  2. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-8fe3323d05b246749d496264ffd29609
Source dataset
uspto-grants-2007_10
Patent number
US07288547B2

Linked notes

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