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Sulfuric Acid → (RS)-S-(4-{[5-bromo-4-(isopropylamino)pyrimidin-2-yl]amino}phenyl)-S-methyl sulfoximide

HRID 1891056
Notes
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Reaction equation

HRID 1891056 reaction equation
[Br:1][C:2]1[C:3]([NH:18][CH:19]([CH3:21])[CH3:20])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:17])=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[N-:22]=[N+]=[N-].[Na+].S(=O)(=O)(O)O.[OH-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[C:3]([NH:18][CH:19]([CH3:21])[CH3:20])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([S:15]([CH3:17])(=[NH:22])=[O:16])=[CH:13][CH:14]=2)=[N:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 596740175-bromo-N4-isopropyl-N2-[4-(methylsulfinyl)phenyl)-pyrimidine-2,4-diamine

Product 1

HCID 59674001(RS)-S-(4-{[5-bromo-4-(isopropylamino)pyrimidin-2-yl]amino}phenyl)-S-methyl sulfoximide

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
45 °C

Procedure

185 mg (0.50 mmol) of (RS)-5-bromo-N4-isopropyl-N2-[4-(methyl sulfinyl)phenyl]-pyrimidine-2,4-diamine in 1 ml of DCM is mixed with 40 mg (0.55 mmol) of sodium azide. The batch is slowly mixed with 0.13 ml of concentrated sulfuric acid at 0° C. and then heated to 45° C. After 16 hours, the batch is cooled to room temperature, mixed with 2 ml of 1N NaOH solution and extracted from ethyl acetate. The combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. The remaining residue is purified by chromatography (DCM/EtOH 9:1). 38 mg (0.10 mmol, corresponding to 20% of theory) of the product is obtained.

Workup

  1. temperaturethe batch is cooled to room temperature
  2. extractionextracted from ethyl acetate
  3. dry with materialThe combined organic phases are dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. customThe remaining residue is purified by chromatography (DCM/EtOH 9:1)
  7. custom38 mg (0.10 mmol, corresponding to 20% of theory) of the product is obtained

Sources & evidence

ORD record
ord-7ac20edddc9f482ab90dd35098a92b09
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08507510B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes