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US 8,895,729 B2Granted
Process for making thienopyrimidine compounds
AssigneeGenentech, Inc.
InventorsSrinivasan Babu, Zhigang Cheng, Francis Gosselin, Pirmin Hidber, Ursula Hoffmann, Theresa Humphries, Reinhard Reents, Qingping Tian, Herbert Yajima
Life of this patent
Estimating the term…
Abstract
Process methods for making the dual mTOR/PI3K inhibitor GDC-0980, named as (S)-1-(4-((2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-hydroxypropan-1-one, having the structure: and stereoisomers, geometric isomers, tautomers, and pharmaceutically acceptable salts thereof.
Claims15
A process for preparing (S)-1-(4-((2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-hydroxypropan-1-one I, having the structure:
- and stereoisomers, geometric isomers, tautomers, and pharmaceutically acceptable salts thereof, comprising:
- (a) reacting a salt of (S)-2-hydroxy-1-(piperazin-1-yl)propan-1-one 6 and 2-chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde IV with a reducing agent to give (S)-1-(4-((2-chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-hydroxypropan-1-one II
- and
- (b) reacting II, a palladium catalyst, and 2-aminopyrimidin-5-ylboronic acid III having the structure:
- to give I.
2 more elements
Dependencies are inferred from the claim text.