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

HRID 1169770Notes

Reaction equation

HRID 1169770 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:32])[NH:29][CH2:30][CH3:31])=[O:26])=[CH:21][CH:20]=1>>[CH2:30]([NH:29][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:32])[CH3:31]

Participants

3

Reactant 2

HCID 58985641(R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)propan-1-olHCID 59550862HCID 59550862, compound

Product 1

HCID 58985731(RS)-N-(ethylcarbamoyl)-S-(4-{[4-{[(R)-2-hydroxy-1-methylethyl]amino}-5-(2-thienyl)pyrimidine-2-yl]amino}phenyl)-S-methylsulfoximideYield 26%

Procedure

In the reaction of (R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)propan-1-ol (296.3 mg, 1.1 mmol) with (RS)—S-(4-aminophenyl)-N-(ethylcarbamoyl)-S-methylsulphoximide (241 mg, 1 mmol) according to procedure 5c, the desired product is obtained in 26% yield (133 mg) after chromatographic purification (silica gel, dichloromethane/ethanol (0%-20% ethanol)).

Sources & evidence

ORD record
ord-5fc1cf128e6e465f874a25de9ca8d460
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

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