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

HRID 1169780Notes

Reaction equation

HRID 1169780 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][CH2:28][CH2:29][O:30][CH3:31])=[O:26])=[CH:21][CH:20]=1>>[CH3:31][O:30][CH2:29][CH2:28][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)([CH3:32])=[O:26]

Participants

3

Reactant 2

HCID 58985641(R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)propan-1-olHCID 59550833(RS)-S-(4-aminophenyl)-N-(2-methoxy-ethyl)-S-methylsulfoximide

Product 1

HCID 58985732(RS)-N-(2-methoxy-ethyl)-S-(4-{[4-{[(R)-2-hydroxy-1-methylethyl]amino}-5-(2-thienyl)pyrimidine-2-yl]amino}phenyl)-S-methylsulfoximideYield 3%

Procedure

In the reaction of (R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)propan-1-ol (248.2 mg, 0.92 mmol) with (RS)—S-(4-aminophenyl)-N-(2-methoxy-ethyl)-S-methylsulphoximide (191 mg, 0.84 mmol) according to procedure 5c, the desired product is obtained in 3% yield (10 mg) after chromatographic purification (silica gel, dichloromethane/ethanol (0%-20% ethanol) and HPLC).

Sources & evidence

ORD record
ord-8a2539b64b2a4039ac0246e36e17bb4c
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

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