(Rs)-s-(4-amino-2-bromphenyl)-n-(ethoxycarbonyl)-s-methylsulfoximide → (Rs)-s-{2-bromo-4-[(4-{[(r)-1-(hydroxymethyl)propyl]amino}-5-(3-thienyl)pyrimidine-2-yl)amino]phenyl}-n-(ethoxycarbonyl)-s-methylsulfoximide

HRID 1169760Notes

Reaction equation

HRID 1169760 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]([CH2:12][CH3:13])[CH2:10][OH:11])[C:5]([C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)=[CH:4][N:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH3:34])(=[N:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:27])=[C:22]([Br:35])[CH:21]=1>>[Br:35][C:22]1[CH:21]=[C:20]([NH:19][C:2]2[N:7]=[C:6]([NH:8][C@@H:9]([CH2:10][OH:11])[CH2:12][CH3:13])[C:5]([C:14]3[CH:18]=[CH:17][S:16][CH:15]=3)=[CH:4][N:3]=2)[CH:25]=[CH:24][C:23]=1[S:26]([CH3:34])(=[N:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:27]

Participants

3

Reactant 2

HCID 59550843(Rs)-s-(4-amino-2-bromphenyl)-n-(ethoxycarbonyl)-s-methylsulfoximideHCID 87440034(r)-2-(2-Chloro-5-thiophen-3-yl-pyrimidine-4-ylamino)-butan-1-ol

Product 1

HCID 58985744(Rs)-s-{2-bromo-4-[(4-{[(r)-1-(hydroxymethyl)propyl]amino}-5-(3-thienyl)pyrimidine-2-yl)amino]phenyl}-n-(ethoxycarbonyl)-s-methylsulfoximideYield 30%

Procedure

In the reaction of (R)-2-(2-chloro-5-thiophen-3-yl-pyrimidine-4-ylamino)-butan-1-ol (426 mg, 1.5 mmol) with (RS)—S-(4-amino-2-bromphenyl)-N-(ethoxycarbonyl)-S-methylsulfoximide (404 mg, 1.3 mmol) according to procedure 5b, the desired product is obtained in 30% yield (214 mg) after chromatographic purification (silica gel, dichloromethane/ethanol (0%-15% ethanol)).

Sources & evidence

ORD record
ord-32a2480527d442fd8ca71266b6bfc0d9
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

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