(R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)butan-1-ol → (Rs)-s-{2-bromo-4-[(4-{[(r)-1-(hydroxymethyl)propyl]amino}-5-(2-thienyl)pyrimidine-2-yl)amino]phenyl}-n-(ethoxycarbonyl)-s-methyl-sulfoximide

HRID 1169761Notes

Reaction equation

HRID 1169761 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[S:15][CH:16]=[CH:17][CH:18]=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[S:15][CH:16]=[CH:17][CH:18]=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 58985648(R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)butan-1-olHCID 59550843(Rs)-s-(4-amino-2-bromphenyl)-n-(ethoxycarbonyl)-s-methylsulfoximide

Product 1

HCID 24769458(Rs)-s-{2-bromo-4-[(4-{[(r)-1-(hydroxymethyl)propyl]amino}-5-(2-thienyl)pyrimidine-2-yl)amino]phenyl}-n-(ethoxycarbonyl)-s-methyl-sulfoximideYield 47%

Procedure

In the reaction of (R)-2-(2-chloro-5-thiophen-2-yl-pyrimidine-4-ylamino)-butan-1-ol (425 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 47% yield (340 mg) after chromatographic purification (silica gel, dichloromethane/ethanol (0%-20% ethanol)).

Sources & evidence

ORD record
ord-ef0b8259f1b84b95bd160fcb303e2899
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

Loading…