Sodium ethoxide → (Rs)-s-ethyl-s-(4-{[4-{[(s)-1-(hydroxymethyl)-3-methylbutyl]amino}-5-(3-thienyl)pyrimidine-2-yl]amino}phenyl)sulfoximide

HRID 1169788Notes

Reaction equation

HRID 1169788 reaction equation
C(OC([N:6]=[S:7]([CH2:35][CH3:36])([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:21]=[C:20]([NH:22][C@H:23]([CH2:28][OH:29])[CH2:24][CH:25]([CH3:27])[CH3:26])[C:19]([C:30]3[CH:34]=[CH:33][S:32][CH:31]=3)=[CH:18][N:17]=2)=[CH:11][CH:10]=1)=[O:8])=O)C.CC[O-].[Na+]>>[CH2:35]([S:7]([C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]2[N:21]=[C:20]([NH:22][C@H:23]([CH2:28][OH:29])[CH2:24][CH:25]([CH3:27])[CH3:26])[C:19]([C:30]3[CH:34]=[CH:33][S:32][CH:31]=3)=[CH:18][N:17]=2)=[CH:13][CH:14]=1)(=[NH:6])=[O:8])[CH3:36]

Participants

3

Reactant 2

HCID 2723922Sodium ethoxideHCID 58985750(RS)-N-(ethoxycarbonyl)-S-ethyl-S-(4-{[4-{[(S)-1-(hydroxymethyl)-3-methyl-butyl]amino}-5-(3-thienyl)pyrimidine-2-yl]amino}phenyl)sulfoximide

Product 1

HCID 58985624(Rs)-s-ethyl-s-(4-{[4-{[(s)-1-(hydroxymethyl)-3-methylbutyl]amino}-5-(3-thienyl)pyrimidine-2-yl]amino}phenyl)sulfoximideYield 34%

Procedure

In the reaction of (RS)—N-(ethoxycarbonyl)-S-ethyl-S-(4-{[4-{[(S)-1-(hydroxy-methyl)-3-methylbutyl]amino}-5-(3-thienyl)pyrimidine-2-yl]amino}phenyl)-sulfoximide (265 mg, 0.50 mmol) with sodium ethylate (70 mg, 1.0 mmol) according to procedure 14, the desired product is obtained in 34% yield (77 mg) after chromatographic purification (silica gel, dichloromethane/methanol (9/1)).

Sources & evidence

ORD record
ord-2a42de7d327548df982c3384d9fea114
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

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