Oxygen → 6-(2,6-Dimethoxy-phenyl)-2-methylsulfanyl-pyrimidine-4-carboxylic acid amide

HRID 68303

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1B(O)O.O=O.Cl[C:17]1[N:22]=[C:21]([S:23][CH3:24])[N:20]=[C:19]([C:25]([NH2:27])=[O:26])[CH:18]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.COCCOC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[C:17]1[N:22]=[C:21]([S:23][CH3:24])[N:20]=[C:19]([C:25]([NH2:27])=[O:26])[CH:18]=1

Komponenten

Reaktionsbedingungen

Temperatur: 75 °C

Versuchsvorschrift

A 7 mL teflon-faced screw-cap vial was charged with 2,6-dimethoxyphenyl-boronic acid (218 mg, 1.2 mmol, 2 eq.) and dichloro-bis-(diphenylphosphinoferrocene)-palladium-dichloromethane adduct (49 mg, 60 μmol, 10 mol %). In a glove box under a nitrogen atmosphere (O2 content<=0.5%), the vial was charged with a solution of the 6-chloro-2-methylsulfanyl-pyrimidine-4-carboxylic acid amide (122 mg, 0.6 mmol) in degassed DMF/DME (1/1, 4.5 mL), and a degassed aqueous 1 M solution of potassium phosphate (1.0 mL, 1 mmol, 1.7 eq.). The vial was sealed, withdrawn from the glove box, and agitated in an incubator shaker at 75° C. for 16 hours. The cooled mixture was then diluted with chloroform (15 mL), and washed with brine (20 mL, 2×10 mL), and aqueous 1 M potassium carbonate (10 mL). The organic layer (solution of 6-(2,6-dimethoxy-phenyl)-2-methylsulfanyl-pyrimidine-4-carboxylic acid amide in chloroform) was then used directly in the next step.

Aufarbeitung

customThe vial was sealed
customwithdrawn from the glove box
additionThe cooled mixture was then diluted with chloroform (15 mL)
washwashed with brine (20 mL, 2×10 mL), and aqueous 1 M potassium carbonate (10 mL)

Quellen und Nachweise

ORD-Eintrag: ord-92d88e080b0e411eb78625e6bd72b495
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08822451B2

Verknüpfte Notizen

Wird geladen…