(R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)butan-1-ol → (RS)-N-(ethoxycarbonyl)-S-(4-{[4-{[(R)-1-(hydroxymethyl)propyl]amino}-5-(2-thienyl)pyrimidine-2-yl]amino}phenyl)-S-cyclopropylsulfoximide

HRID 1169767Notes

Reaction equation

HRID 1169767 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]([CH2:12][CH3:13])[CH2:10][OH:11])[C:5]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[CH:4][N:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([C:34]2[CH:39]=[CH:38]C=CC=2)(=[N:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:27])=[CH:22][CH:21]=1>>[CH2:32]([O:31][C:29]([N:28]=[S:26]([C:23]1[CH:22]=[CH:21][C:20]([NH:19][C:2]2[N:7]=[C:6]([NH:8][C@@H:9]([CH2:10][OH:11])[CH2:12][CH3:13])[C:5]([C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)=[CH:4][N:3]=2)=[CH:25][CH:24]=1)([CH:34]1[CH2:39][CH2:38]1)=[O:27])=[O:30])[CH3:33]

Participants

3

Reactant 2

HCID 58985648(R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)butan-1-olHCID 59550854(RS)-S-(4-aminophenyl)-N-(ethoxycarbonyl)-S-phenylsulfoximide

Product 1

HCID 86615481(RS)-N-(ethoxycarbonyl)-S-(4-{[4-{[(R)-1-(hydroxymethyl)propyl]amino}-5-(2-thienyl)pyrimidine-2-yl]amino}phenyl)-S-cyclopropylsulfoximideYield 49%

Procedure

In the reaction of (R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)butan-1-ol (151 mg, 0.53 mmol) with (RS)—S-(4-aminophenyl)-N-(ethoxycarbonyl)-S-phenylsulfoximide (147 mg, 0.48 mmol) according to procedure 5c, the desired product is obtained in 49% yield (130 mg) after chromatographic purification (silica gel, dichloromethane/ethanol (0%-20% ethanol)).

Sources & evidence

ORD record
ord-8f016364967945b4a65b7582c0c3dee0
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

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