Tetrabutylammonium Fluoride → (RS)-S-[4-({5-bromo-4-[(R)-(2-hydroxy-1,2-dimethylpropyl)amino]pyrimidin-2-yl}amino)phenyl]-S-cyclopropylsulfoximide

HRID 1391439Notes

Reaction equation

HRID 1391439 reaction equation
[Br:1][C:2]1[C:3]([NH:30][C@H:31]([CH3:36])[C:32]([OH:35])([CH3:34])[CH3:33])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH:27]3[CH2:29][CH2:28]3)(=[N:17]S(CC[Si](C)(C)C)(=O)=O)=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Br:1][C:2]1[C:3]([NH:30][C@H:31]([CH3:36])[C:32]([OH:35])([CH3:33])[CH3:34])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH:27]3[CH2:28][CH2:29]3)(=[NH:17])=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59674047(RS)-S-[4-({5-bromo-4-[(R)-(2-hydroxy-1,2-dimethylpropyl)amino]-pyrimidin-2-yl}amino)phenyl]-S-cyclopropyl-N-[2-(trimethylsilyl)ethylsulfonyl]-sulfoximide

Product 1

HCID 59674027(RS)-S-[4-({5-bromo-4-[(R)-(2-hydroxy-1,2-dimethylpropyl)amino]pyrimidin-2-yl}amino)phenyl]-S-cyclopropylsulfoximide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

50 mg of (RS)-S-[4-({5-bromo-4-[(R)-(2-hydroxy-1,2-dimethylpropyl)amino]-pyrimidin-2-yl}amino)phenyl]-S-cyclopropyl-N-[2-(trimethylsilyl)ethylsulfonyl]-sulfoximide is dissolved in 1 ml of tetrahydrofuran and mixed with 0.3 ml of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran. The mixture is stirred for 3 days at 50° C. and purified by flash chromatography (dichloromethane-dichloromethane/ethanol 9:1). 10 mg (28% of theory) of the product is obtained.

Workup

  1. custompurified by flash chromatography (dichloromethane-dichloromethane/ethanol 9:1)
  2. custom10 mg (28% of theory) of the product is obtained

Sources & evidence

ORD record
ord-baa6d63d296b48bd85caaba639f8ad39
Source dataset
uspto-grants-2008_03
Patent number
US07338958B2

Reaction notes

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