Ethyl [(4-aminophenyl)(methyl)oxido-sulfanylidene]carbamate → (RS)-N-(ethoxycarbonyl)-S-(4-{[4-{[(R)-2-hydroxy-1-methylethyl]amino}-5-(2-thienyl)pyrimidine-2-yl]amino}phenyl)-S-methylsulfoximide

HRID 1169755Notes

Reaction equation

HRID 1169755 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]([CH3:12])[CH2:10][OH:11])[C:5]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[CH:4][N:3]=1.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:33])(=[N:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:26])=[CH:21][CH:20]=1>>[CH2:31]([O:30][C:28]([N:27]=[S:25]([C:22]1[CH:21]=[CH:20][C:19]([NH:18][C:2]2[N:7]=[C:6]([NH:8][C@H:9]([CH3:12])[CH2:10][OH:11])[C:5]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[CH:4][N:3]=2)=[CH:24][CH:23]=1)([CH3:33])=[O:26])=[O:29])[CH3:32]

Participants

3

Reactant 2

HCID 44122615Ethyl [(4-aminophenyl)(methyl)oxido-sulfanylidene]carbamateHCID 58985641(R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)propan-1-ol

Product 1

HCID 58985742(RS)-N-(ethoxycarbonyl)-S-(4-{[4-{[(R)-2-hydroxy-1-methylethyl]amino}-5-(2-thienyl)pyrimidine-2-yl]amino}phenyl)-S-methylsulfoximideYield 27%

Procedure

In the reaction of (R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)propan-1-ol (178 mg, 0.7 mmol) with (RS)—S-(4-aminophenyl)-N-(ethoxycarbonyl)-S-methyl-sulfoximide (145 mg, 0.6 mmol) according to procedure 5a, the desired product is obtained in 27% yield (85 mg) after chromatographic purification (silica gel, ethyl acetate/hexane (0%-80% ethyl acetate)).

Sources & evidence

ORD record
ord-d886da4e8a8743ada02b7b5e04c25da1
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

Loading…