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

HRID 1169787Notes

Reaction equation

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

Participants

Reactant 2

HCID 2723922Sodium ethoxide

HCID 58985754(RS)-N-(ethoxycarbonyl)-S-(4-{[4-{[(S)-1-(hydroxymethyl)-3-methylbutyl]amino}-5-(3-thienyl)pyrimidine-2-yl]amino}phenyl)-S-methylsulfoximide

Product 1

HCID 58985584(Rs)-s-(4-{[4-{[(s)-1-(hydroxymethyl)-3-methylbutyl]amino}-5-(3-thienyl)-pyrimidine-2-yl]amino}phenyl)-s-methylsulfoximideYield 36%

Procedure

In the reaction of (RS)—N-(ethoxycarbonyl)-S-(4-{[4-{[(S)-1-(hydroxymethyl)-3-methylbutyl]amino}-5-(3-thienyl)pyrimidine-2-yl]amino}phenyl)-S-methyl-sulfoximide (135 mg, 0.26 mmol) with sodium ethylate (70 mg, 1.0 mmol) according to procedure 14, the desired product is obtained in 36% yield (42 mg) after chromatographic purification (silica gel, dichloromethane/methanol (9/1)).

Sources & evidence

ORD record: ord-298c97a68e394de999a66bc11b65a0ce
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825128B2

Reaction notes

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