(R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)propan-1-ol → HCID 58985733, compound

HRID 1169769Notes

Reaction equation

HRID 1169769 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]([CH3:32])(=[N:27][C:28](=[O:31])[NH:29][CH3:30])=[O:26])=[CH:21][CH:20]=1>>[CH3:30][NH:29][C:28]([N:27]=[S:25]([C:22]1[CH:23]=[CH:24][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:20][CH:21]=1)([CH3:32])=[O:26])=[O:31]

Participants

3

Reactant 2

HCID 58985641(R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)propan-1-olHCID 59550841(RS)-S-(4-aminophenyl)-N-(methylcarbamoyl)-S-methylsulfoximide

Product 1

HCID 58985733HCID 58985733, compoundYield 23.5%

Procedure

In the reaction of (R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)propan-1-ol (164.5 mg, 0.61 mmol) with (RS)—S-(4-aminophenyl)-N-(methylcarbamoyl)-S-methylsulphoximide (126 mg, 0.55 mmol) according to procedure 5c, the desired product is obtained in 23.5% yield (60 mg) after chromatographic purification (silica gel, dichloromethane/ethanol (0%-20% ethanol)).

Sources & evidence

ORD record
ord-8cf661f350bd4209b5864bc61bcf3f3c
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

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