Pfizer Corporation

Jennifer L Rutherford

Joel Michael Hawkins

Frank J Urban

Sally Gut Ruggeri

Teresa M Makowski

This invention relates to methods and intermediates useful for the synthesis of pyrrolo[2,3-d]pyrimidine compounds. Specifically novel synthetic methods and intermediates for the synthesis of 3-{(3R,4R)-4-methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino}-piperidin-1-yl)-3-oxo-propionitrile and its corresponding citrate salt are disclosed.

Pyrrolo[2,3-d]pyrimidine derivatives: their intermediates and synthesis

Pyrrolo[2,3-d]pyrimidine derivatives; their intermediates and synthesis

This invention relates to a new process for the preparation of novel substituted haloarene compounds of the formula I or IV: respectively, wherein R, R, R, R, R, X, and Y are as defined herein, that comprises a novel and efficient selective mono-lithiation of a dihaloarene of the formula II or V: respectively, by an organo-lithium compound in the presence of a carbonyl reactant of the formula III: wherein Rand Rare as defined herein. In the process of the instant invention, the newly formed lithiated haloarene is sequentially quenched in situ by the carbonyl reactant to form said substituted haloarene. The process is suitable for batch or continuous flow systems. The substituted haloarenes produced by the process of the present invention are useful intermediates in the preparation of N-aryl or N-heteroaryl substituted pharmaceutically active compounds that include selective antagonists, inverse agonists and partial agonists of serotonin 1 (5-HT) receptors useful in treating or preventing depression, anxiety, obsessive compulsive disorder (OCD) and other disorders for which a 5-HTagonist or antagonist is indicated.

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Easton, PA, United States of America

Jennifer L Rutherford