Hydrochloric Acid → (RS)-S-[3-({5-bromo-4-[(R)-(2-hydroxy-1,2-dimethylpropyl)amino]pyrimidin-2-yl}amino)phenyl]-S-methyl sulfoximide

HRID 1891049Notes

Reaction equation

HRID 1891049 reaction equation
[Br:1][C:2]1[C:3]([NH:9][C@H:10]([CH3:15])[C:11]([CH3:14])([OH:13])[CH3:12])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH2:16][C:17]1[CH:18]=[C:19]([S:23]([CH3:26])(=[NH:25])=[O:24])[CH:20]=[CH:21][CH:22]=1.Cl>C(#N)C.O1CCOCC1>[Br:1][C:2]1[C:3]([NH:9][C@H:10]([CH3:15])[C:11]([OH:13])([CH3:14])[CH3:12])=[N:4][C:5]([NH:16][C:17]2[CH:18]=[C:19]([S:23]([CH3:26])(=[NH:25])=[O:24])[CH:20]=[CH:21][CH:22]=2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 59674068(R)-3-(5-bromo-2-chloropyrimidin-4-ylamino)-2-methylbutan-2-olHCID 59674075851008-24-7

Product 1

HCID 59673989(RS)-S-[3-({5-bromo-4-[(R)-(2-hydroxy-1,2-dimethylpropyl)amino]pyrimidin-2-yl}amino)phenyl]-S-methyl sulfoximide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

127 mg (0.43 mmol) of (R)-3-[(5-bromo-2-chloropyrimidin-4-yl)amino]-2-methyl-butan-2-ol in 1 ml of acetonitrile is added to 74 mg (0.43 mmol) of (RS)—S-(3-aminophenyl)-S-methyl sulfoximide in 0.5 ml of acetonitrile. It is mixed with 0.1 ml of a 4N solution of HCl in dioxane, and the batch is refluxed overnight. The solvent is drawn off, and the remaining residue is purified by chromatography (DCM/EtOH 9:1). 37 mg (0.09 mmol, corresponding to 20% of theory) of the product is obtained.

Workup

  1. temperaturethe batch is refluxed overnight
  2. customthe remaining residue is purified by chromatography (DCM/EtOH 9:1)
  3. custom37 mg (0.09 mmol, corresponding to 20% of theory) of the product is obtained

Sources & evidence

ORD record
ord-d90c49b4468b42cb8b9f7d05c1ec5df7
Source dataset
uspto-grants-2013_08
Patent number
US08507510B2

Reaction notes

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