3-(Chloromethyl)pyridine hydrochloride → 6-ethyl-4-(3-pyridylmethyl)-[1,2,5]oxadiazolo[3,4-d]pyrimidine-5,7(4H,6H)-dione-1-oxide

HRID 1769596

Reaktionsgleichung

[H-].[Li+].[CH2:3]([N:5]1[C:10](=[O:11])[C:9]2=[N+:12]([O-:15])[O:13][N:14]=[C:8]2[NH:7][C:6]1=[O:16])[CH3:4].Cl.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24]Cl)[CH:19]=1>CN(C=O)C>[CH2:3]([N:5]1[C:10](=[O:11])[C:9]2=[N+:12]([O-:15])[O:13][N:14]=[C:8]2[N:7]([CH2:24][C:20]2[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=2)[C:6]1=[O:16])[CH3:4]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

0.48 g (60 mmol) of lithium hydride is added in portions to a solution of 5.0 g (25 mmol) of 6-ethyl-[1,2,5]oxadiazolo[3,4-d]pyrimidine-5,7(4H,6H)-dione-1-oxide in 250 ml of DMF. The mixture is heated at 60° C. for 15 minutes, then 4.9 g (30 mmol) of 3-picolyl chloride hydrochloride are added and the mixture is heated at 80° C. for 3 hours. It is then largely concentrated, the residue is taken up with ethyl acetate and the mixture is extracted with 10% strength hydrochloric acid. The aqueous extract is neutralised and extracted with ethyl acetate. Relatively readily volatile impurities are removed by distillation in vacuo at 100° C./0.5 mm Hg and the residue is chromatographed. 1.4 g (20%) of 6-ethyl-4-(3-pyridylmethyl)-[1,2,5]oxadiazolo[3,4-d]pyrimidine-5,7(4H,6H)-dione-1-oxide are obtained as a highly viscous oil.

Aufarbeitung

temperaturethe mixture is heated at 80° C. for 3 hours
concentrationIt is then largely concentrated
extractionthe mixture is extracted with 10% strength hydrochloric acid
extractionThe aqueous extract
extractionextracted with ethyl acetate
customRelatively readily volatile impurities are removed by distillation in vacuo at 100° C./0.5 mm Hg
customthe residue is chromatographed

Quellen und Nachweise

ORD-Eintrag: ord-a1c5d655e4234b35a21616054a292e2a
Quelldatensatz: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05382585

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