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

HRID 1891051Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:16])(=[N:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9])=[CH:4][CH:3]=1.[Br:17][C:18]1[C:19]([NH:25][C@H:26]([CH3:31])[C:27]([CH3:30])([OH:29])[CH3:28])=[N:20][C:21](Cl)=[N:22][CH:23]=1.O.Cl>C(#N)C.O1CCOCC1>[Br:17][C:18]1[C:19]([NH:25][C@H:26]([CH3:31])[C:27]([OH:29])([CH3:28])[CH3:30])=[N:20][C:21]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([S:8]([CH3:16])(=[N:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9])=[CH:4][CH:3]=2)=[N:22][CH:23]=1

Participants

Conditions

Temperature: 60 °C

Procedure

600 mg (2.48 mmol) of (RS)—S-(4-aminophenyl)-N-(ethoxycarbonyl)-S-methyl sulfoximide and 610 mg (2.07 mmol) of (R)-3-[(5-bromo-2-chloropyrimidin-4-yl)amino]-2-methyl-butan-2-ol in 8 ml of acetonitrile are mixed with 0.52 ml of water and 0.52 ml of a 4N solution of HCl in dioxane. The batch is stirred for 24 hours at 60° C. and then concentrated by evaporation. The remaining residue is purified by chromatography (DCM/EtOH 8:2). 649 mg (1.30 mmol, corresponding to 53% of theory) of the product is obtained.

Workup

concentrationconcentrated by evaporation
customThe remaining residue is purified by chromatography (DCM/EtOH 8:2)
custom649 mg (1.30 mmol, corresponding to 53% of theory) of the product is obtained

Sources & evidence

ORD record: ord-a0e37b4d23d346258fe375425f39c72a
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507510B2

Reaction notes

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