Ethyl [(4-aminophenyl)(methyl)oxido-sulfanylidene]carbamate → (RS)-N-(ethoxycarbonyl)-S-[4-({4-[(2-hydroxyethyl)amino]-5-(2-thienyl)-pyrimidine-2-yl}amino)phenyl]-S-methylsulfoximide

HRID 1169756Notes

Reaction equation

HRID 1169756 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][OH:11])[C:5]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[CH:4][N:3]=1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([CH3:32])(=[N:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:25])=[CH:20][CH:19]=1>>[CH2:30]([O:29][C:27]([N:26]=[S:24]([C:21]1[CH:20]=[CH:19][C:18]([NH:17][C:2]2[N:7]=[C:6]([NH:8][CH2:9][CH2:10][OH:11])[C:5]([C:12]3[S:13][CH:14]=[CH:15][CH:16]=3)=[CH:4][N:3]=2)=[CH:23][CH:22]=1)([CH3:32])=[O:25])=[O:28])[CH3:31]

Participants

3

Reactant 2

HCID 44122615Ethyl [(4-aminophenyl)(methyl)oxido-sulfanylidene]carbamateHCID 589857042-(2-Chloro-5-(2-thienyl)pyrimidine-4-ylamino)ethanol

Product 1

HCID 58985671(RS)-N-(ethoxycarbonyl)-S-[4-({4-[(2-hydroxyethyl)amino]-5-(2-thienyl)-pyrimidine-2-yl}amino)phenyl]-S-methylsulfoximideYield 37%

Procedure

In the reaction of 2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)ethanol (200 mg, 0.8 mmol) with (RS)—S-(4-aminophenyl)-N-(ethoxycarbonyl)-S-methyl-sulfoximide (173 mg, 0.7 mmol) according to procedure 5a, the desired product is obtained in 37% yield (120 mg) after chromatographic purification (silica gel, dichloromethane/methanol (0%-20% methanol)).

Sources & evidence

ORD record
ord-f499fba778994273b8a9033ac9fbe18f
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

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