Preparation of 2-amino-7-(1-substituted-2-hydroxyethyl)-3, 5-dihydropyrrolo[3,2-d]pyrimidin-4-ones

US6043365A · kind A · utility

Assignee

• Novartis AG · CH

Inventors

• Leslie Wighton McQuire · Hackettstown, US
• Benjamin Mugrage · Berkeley Heights, US
• Mahavir Prashad · East Hanover, US
• John H. van Duzer · Phillipsburg, US

Key dates

• Filing date: May 28, 1998
• Grant date: Mar 28, 2000
• Expiry date: May 28, 2018

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The compounds of formula I ##STR1## wherein Ar represents biaryl, carbocyclic or heterocyclic aryl, are prepared, as substantially pure enantiomers, by PA1 (a) condensing a compound of the formula ##STR2## as a substantially pure enantiomer, wherein Ar has meaning as defined above and R.sub.6 is on O-protecting group with a lower alkyl ester of formic acid; PA1 (b) then condensing the compound so obtained with a compound of the formula ##STR3## wherein R.sub.8 is hydrogen or COOR.sub.3 and R.sub.3 is lower alkyl; (c) then cyclizing the compound so obtained to a compound of the formula ##STR4## as a substantially pure enantiomer; (d) and then condensing the compound so obtained PA2 (1) with a carbocyclic aroyl isothiocyanate and treatment of the product so obtained with an alkyl halide followed by anhydrous ammonia; or PA2 (2) with cyanamide in acid, optionally followed by treatment with a base.