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

HRID 1891056Notes

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

Participants

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

temperaturethe batch is cooled to room temperature
extractionextracted from ethyl acetate
dry with materialThe combined organic phases are dried (Na2SO4)
filtrationfiltered
concentrationconcentrated by evaporation
customThe remaining residue is purified by chromatography (DCM/EtOH 9:1)
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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