(S)-2-(2-chloro-5-thiophen-3-yl-pyrimidine-4-ylamino)-4-methyl-pentan-1-ol → (RS)-N-(ethoxycarbonyl)-S-ethyl-S-(4-{[4-{[(S)-1-(hydroxymethyl)-3-methyl-butyl]amino}-5-(3-thienyl)pyrimidine-2-yl]amino}phenyl)sulfoximide

HRID 1169759Notes

Reaction equation

HRID 1169759 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:10][OH:11])[C:5]([C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)=[CH:4][N:3]=1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([CH2:36][CH3:37])(=[N:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:29])=[CH:24][CH:23]=1>>[CH2:34]([O:33][C:31]([N:30]=[S:28]([CH2:36][CH3:37])([C:25]1[CH:26]=[CH:27][C:22]([NH:21][C:2]2[N:7]=[C:6]([NH:8][C@H:9]([CH2:10][OH:11])[CH2:12][CH:13]([CH3:15])[CH3:14])[C:5]([C:16]3[CH:20]=[CH:19][S:18][CH:17]=3)=[CH:4][N:3]=2)=[CH:23][CH:24]=1)=[O:29])=[O:32])[CH3:35]

Participants

3

Reactant 2

HCID 58985746(S)-2-(2-chloro-5-thiophen-3-yl-pyrimidine-4-ylamino)-4-methyl-pentan-1-olHCID 59673998Benzenamine, 4-[N-(Ethoxycarbonyl)-S-Ethylsulfonimidoyl]

Product 1

HCID 58985750(RS)-N-(ethoxycarbonyl)-S-ethyl-S-(4-{[4-{[(S)-1-(hydroxymethyl)-3-methyl-butyl]amino}-5-(3-thienyl)pyrimidine-2-yl]amino}phenyl)sulfoximideYield 59%

Procedure

In the reaction (S)-2-(2-chloro-5-thiophen-3-yl-pyrimidine-4-ylamino)-4-methyl-pentan-1-ol (312 mg, 1.00 mmol) with (RS)—S-(4-amino-phenyl)-N-(ethoxycarbonyl)-S-ethylsulfoximide (231 mg, 0.90 mmol) according to procedure 5b, the desired product is obtained in 59% yield (282 mg) after chromatographic purification (silica gel, dichloromethane/methanol (0%-10% methanol)).

Sources & evidence

ORD record
ord-96a295fcae9c4c1985687e68c9a41f34
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

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