Triethylamine → (RS)-S-[4-({5-bromo-4-[(RS)-(1-hydroxymethyl-propyl)sulfanyl]pyrimidin-2-yl}amino)phenyl]-S-methyl Sulfoximide

HRID 1891058Notes

Reaction equation

HRID 1891058 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[NH:17])=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.C(N(CC)CC)C.[SH:27][CH:28]([CH2:31][CH3:32])[CH2:29][OH:30]>CN(C)C=O>[Br:1][C:2]1[C:3]([S:27][CH:28]([CH2:29][OH:30])[CH2:31][CH3:32])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[NH:17])=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14249190(RS)-2-mercapto-butan-1-olHCID 59674032(RS)-S-{4-[(5-bromo-4-chloropyrimidin-2-yl)amino]phenyl}-S-methyl sulfoximide

Product 1

HCID 59674013(RS)-S-[4-({5-bromo-4-[(RS)-(1-hydroxymethyl-propyl)sulfanyl]pyrimidin-2-yl}amino)phenyl]-S-methyl SulfoximideYield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

362 mg of (RS)—S-{4-[(5-bromo-4-chloropyrimidin-2-yl)amino]phenyl}-S-methyl sulfoximide is dissolved in 1.5 ml of dimethylformamide, mixed with 0.5 ml of triethylamine and 320 mg of (RS)-2-mercapto-butan-1-ol and stirred for 18 hours at room temperature. The mixture is evaporated to the dry state in a vacuum and purified by flash chromatography (dichloromethane/ethanol). 255 mg of the product with a melting point of 175-180° C. is obtained.

Workup

  1. customThe mixture is evaporated to the dry state in a vacuum
  2. custompurified by flash chromatography (dichloromethane/ethanol)

Sources & evidence

ORD record
ord-3d26bcd669624636a95ee104bfbda64f
Source dataset
uspto-grants-2013_08
Patent number
US08507510B2

Reaction notes

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