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

HRID 1891048Notes

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]([O:32][C@H:33]([CH3:37])[C@H:34]([OH:36])[CH3:35])=[N:27][C:28](Cl)=[N:29][CH:30]=1>C(#N)C.O1CCOCC1>[Br:24][C:25]1[C:26]([O:32][C@H:33]([CH3:37])[C@H:34]([OH:36])[CH3:35])=[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: 70 °C

Procedure

A solution of 205 mg (0.56 mmol) of (RS)—S-(4-aminophenyl)-S-(2-hydroxyethyl)-N-[2-(trimethylsilyl)ethylsulfonyl]sulfoximide in 2 ml of acetonitrile is mixed with 0.15 ml of a 4N solution of HCl in dioxane. 175 mg (0.62 mmol) of (2R,3R)-3-[(5-bromo-2-chloropyrimidin-4-yl)oxy]-butan-2-ol in 2 ml of acetonitrile is added, and the batch is stirred for 24 hours at 70° C. Then, it is stirred for another 24 hours at 85° C. The solvent is removed, and the remaining residue is purified by chromatography (DCM/EtOH 9:1). 110 mg (0.18 mmol, corresponding to 32% of theory) of the product is obtained.

Workup

stirringThen, it is stirred for another 24 hours at 85° C
customThe solvent is removed
customthe remaining residue is purified by chromatography (DCM/EtOH 9:1)
custom110 mg (0.18 mmol, corresponding to 32% of theory) of the product is obtained

Sources & evidence

ORD record: ord-64ed1e2640024d1098c69c8c19f47a26
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507510B2

Reaction notes

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