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A process for preparing tert-butyl (S)-3-(4-amino-3-(4-phenoxyphenyl)-1Hpyrazolo[ 3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate

IP.com Disclosure Number: IPCOM000236865D
Publication Date: 2014-May-20
Document File: 1 page(s) / 7K

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A process for preparing tert-butyl (S)-3-(4-amino-3-(4-phenoxyphenyl)-1H- pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate

     Provided herein is a process for preparing tert-butyl (S)-3-(4-amino-3-(4- phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate, referred herein as Compound I. The process is described in Example 1.

Compound I may be used for preparing (S)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H- pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one.

Example 1: A process for preparing tert-butyl (S)-3-(4-amino-3-(4- phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate

    A flask equipped with overhead stirrer and reflux condenser was charged with 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (1 g, 3.3 mmol), Cs2CO3
(3.2 g, 9.9 mmol), 10 ml of DMF and 1eq of activated form of tert-butyl (S)-3- hydroxypiperidine-1-carboxylate. The activated form of tert-butyl (S)-3- hydroxypiperidine-1-carboxylate can be: mesylate /tosylate /nosylate /acetate /trifluoroacetate/triflate.

    The reaction was heated up to 100 °C and stirred at this temperature for 24- 48h followed by extraction with EtOAc and water and evaporation of the organic phase.
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine used in the above process may be prepared for example according to the process described in US 6,660,744.