(R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)propan-1-ol → HCID 58985697, compound

HRID 1169776Notes

Reaction equation

HRID 1169776 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]([CH3:38])(=[N:27][C:28](=[O:37])[NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=2)=[O:26])=[CH:21][CH:20]=1>>[Cl:36][C:32]1[CH:31]=[C:30]([NH:29][C:28]([N:27]=[S:25]([C:22]2[CH:21]=[CH:20][C:19]([NH:18][C:2]3[N:7]=[C:6]([NH:8][C@H:9]([CH3:12])[CH2:10][OH:11])[C:5]([C:13]4[S:14][CH:15]=[CH:16][CH:17]=4)=[CH:4][N:3]=3)=[CH:24][CH:23]=2)([CH3:38])=[O:26])=[O:37])[CH:35]=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 58985641(R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)propan-1-olHCID 59550832HCID 59550832, compound

Product 1

HCID 58985697HCID 58985697, compoundYield 26%

Procedure

In the reaction of (R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)propan-1-ol (115.5 mg, 0.43 mmol) with (RS)—S-(4-aminophenyl)-N-(3-chloro-phenylcarbamoyl)-S-methylsulphoximide (126 mg, 0.39 mmol) according to procedure 5c, the desired product is obtained in 26% yield (56 mg) after chromatographic purification (silica gel, dichloromethane/ethanol (0%-20% ethanol)).

Sources & evidence

ORD record
ord-299a2661db504c758fdbc4c7069c11f6
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

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