(R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)propan-1-ol → (S)-N-(ethoxycarbonyl)-S-(4-{[4-{[(R)-2-hydroxy-1-methylethyl]amino}-5-(2-thienyl)pyrimidine-2-yl]amino}phenyl)-S-cyclopropylsulfoximide

HRID 1169763Notes

Reaction equation

HRID 1169763 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]([CH:33]2[CH2:35][CH2:34]2)(=[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)([CH:33]1[CH2:34][CH2:35]1)=[O:26])=[O:29])[CH3:32]

Participants

3

Reactant 2

HCID 58985641(R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)propan-1-olHCID 59550868(S)-S-(4-aminophenyl)-N-(ethoxycarbonyl)-S-cyclo-propyl-sulfoximide

Product 1

HCID 24769514(S)-N-(ethoxycarbonyl)-S-(4-{[4-{[(R)-2-hydroxy-1-methylethyl]amino}-5-(2-thienyl)pyrimidine-2-yl]amino}phenyl)-S-cyclopropylsulfoximideYield 50%

Procedure

In the reaction of (R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)propan-1-ol (267 mg, 1.0 mmol) with (S)—S-(4-aminophenyl)-N-(ethoxycarbonyl)-S-cyclo-propyl-sulfoximide (241 mg, 0.9 mmol) according to procedure 5c, the desired product is obtained in 50% yield (250 mg) after chromatographic purification (silica gel, dichloromethane/ethanol (0%-20% ethanol)).

Sources & evidence

ORD record
ord-4dc7b688d2304b52acdb59293f941a39
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

Loading…