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

HRID 1169789Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([NH:15][C@@H:16]([CH2:19][OH:20])[CH2:17][CH3:18])[C:12]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)=[CH:11][N:10]=2)[CH:5]=[CH:4][C:3]=1[S:26]([CH3:34])(=[N:28]C(OCC)=O)=[O:27].CC[O-].[Na+]>>[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([NH:15][C@@H:16]([CH2:19][OH:20])[CH2:17][CH3:18])[C:12]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)=[CH:11][N:10]=2)[CH:5]=[CH:4][C:3]=1[S:26]([CH3:34])(=[NH:28])=[O:27]

Participants

Reactant 2

HCID 2723922Sodium ethoxide

HCID 24769458(Rs)-s-{2-bromo-4-[(4-{[(r)-1-(hydroxymethyl)propyl]amino}-5-(2-thienyl)pyrimidine-2-yl)amino]phenyl}-n-(ethoxycarbonyl)-s-methyl-sulfoximide

Product 1

HCID 58985563(Rs)-s-{2-bromo-4-[(4-{[(r)-1-(hydroxymethyl)propyl]amino}-5-(2-thienyl)-pyrimidine-2-yl)amino]phenyl}-s-methylsulfoximideYield 64%

Procedure

In the reaction of (RS)—S-{2-bromo-4-[(4-{[(R)-1-(hydroxymethyl)propyl]amino}-5-(2-thienyl)pyrimidine-2-yl)amino]phenyl}-N-(ethoxycarbonyl)-S-methyl-sulfoximide (130 mg, 0.23 mmol) with sodium ethylate (22 mg, 0.31 mmol) according to procedure 14, the desired product is obtained in 64% yield (73 mg) after chromatographic purification (silica gel, dichloromethane/ethanol (9/1)).

Sources & evidence

ORD record: ord-02ad8a940713444ca0b2dd40e12ac91b
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825128B2

Reaction notes

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