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

HRID 1391440Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:20][CH2:21][OH:22])(=[N:10][S:11]([CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])(=[O:13])=[O:12])=[O:9])=[CH:4][CH:3]=1.Cl.[Br:24][C:25]1[C:26]([NH:32][C@H:33]([CH3:38])[C:34]([CH3:37])([OH:36])[CH3:35])=[N:27][C:28](Cl)=[N:29][CH:30]=1>C(#N)C.O.O1CCOCC1>[Br:24][C:25]1[C:26]([NH:32][C@H:33]([CH3:38])[C:34]([OH:36])([CH3:35])[CH3:37])=[N:27][C:28]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([S:8]([CH2:20][CH2:21][OH:22])(=[N:10][S:11]([CH2:14][CH2:15][Si:16]([CH3:18])([CH3:17])[CH3:19])(=[O:12])=[O:13])=[O:9])=[CH:4][CH:3]=2)=[N:29][CH:30]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 200 mg (0.55 mmol) of (RS)-S-(4-aminophenyl)-S-(2-hydroxyethyl)-N-[2-(trimethylsilyl)ethylsulfonyl]sulfoximide in 2 ml of acetonitrile and 0.5 ml of water is mixed with 0.17 ml of a 4N solution of HCl in dioxane. 198 mg (0.67 mmol) of (R)-3-[(5-bromo-2-chloropyrimidin-4-yl)amino]-2-methyl-butan-2-ol in 1.5 ml of acetonitrile is added, and the batch is stirred for 20 hours at 80° C. The solvent is removed, and the remaining residue is purified by chromatography (DCM/EtOH 9: 1). 148 mg (0.24 mmol, corresponding to 44% of theory) of the product is obtained.

Workup

customThe solvent is removed
customthe remaining residue is purified by chromatography (DCM/EtOH 9: 1)
custom148 mg (0.24 mmol, corresponding to 44% of theory) of the product is obtained

Sources & evidence

ORD record: ord-a45f72a03d0042ac9accf16fb6ef87d9
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07338958B2

Reaction notes

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