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Sodium Chloride → (RS)-S-[4-({5-bromo-4-[(R)-(2-hydroxy-1,2-dimethylpropyl)amino]pyrimidin-2-yl}amino)phenyl]-S-methyl Sulfoximide

HRID 1891053
Notes
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Reaction equation

HRID 1891053 reaction equation
[Br:1][C:2]1[C:3]([NH:24][C@H:25]([CH3:30])[C:26]([OH:29])([CH3:28])[CH3:27])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:23])(=[N:17]C(OCC)=O)=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.CC[O-].[Na+].[Na+].[Cl-]>C(O)C>[Br:1][C:2]1[C:3]([NH:24][C@H:25]([CH3:30])[C:26]([OH:29])([CH3:27])[CH3:28])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:23])(=[NH:17])=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 2723922Sodium ethoxideHCID 59674007(RS)-S-[4-({5-bromo-4-[(R)-(2-hydroxy-1,2-dimethylpropyl)amino]pyrimidin-2-yl}amino)phenyl]-N-(ethoxycarbonyl)-S-methyl Sulfoximide

Product 1

HCID 59674034(RS)-S-[4-({5-bromo-4-[(R)-(2-hydroxy-1,2-dimethylpropyl)amino]pyrimidin-2-yl}amino)phenyl]-S-methyl Sulfoximide

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent
2×

Procedure

1.65 g (3.30 mmol) of (RS)—S-[4-({5-bromo-4-[(R)-(2-hydroxy-1,2-dimethylpropyl)amino]pyrimidin-2-yl}amino)phenyl]-N-(ethoxycarbonyl)-S-methyl sulfoximide in 6.5 ml of ethanol is mixed with 19.1 ml (6.69 mmol) of a 0.35 molar solution of NaOEt in ethanol and stirred under reflux for 5 hours. The batch is stirred overnight at room temperature and then added to a saturated NaCl solution. It is extracted with ethyl acetate, and the combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. The remaining residue is purified by chromatography (DCM/EtOH 9:1). 0.95 g (2.22 mmol, corresponding to 67% of theory) of the product is obtained.

Workup

  1. temperatureunder reflux for 5 hours
  2. stirringThe batch is stirred overnight at room temperature
  3. extractionIt is extracted with ethyl acetate
  4. dry with materialthe combined organic phases are dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe remaining residue is purified by chromatography (DCM/EtOH 9:1)
  8. custom0.95 g (2.22 mmol, corresponding to 67% of theory) of the product is obtained

Sources & evidence

ORD record
ord-2a5180f2d1fa4253934cf870fe261aea
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08507510B2

Reaction notes

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