supplementary material synthesis of pyrazolo[1,5-a

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Supplementary Material

Synthesis of pyrazolo[1,5-a]pyrimidine ring as a possible bioisosteric replacement of the 5-(1H-pyrrol-1-yl)pyrazole scaffold

Claudia Mugnaini, Livia Pasculini, Carlotta Pagli, Antonella Brizzi, Marco Paolino, Beatrice Gianibbi, and Federico Corelli*

Department of Biotechnology, Chemistry and Pharmacy, University of Siena, 53100 Siena, Italy

Email: federico.corelli@unisi.it

Table of Contents HPLC/MS traces for compounds 2a-f

Compound 2a ......................................................................................................................................................... S2

Compound 2b......................................................................................................................................................... S4

Compound 2c ......................................................................................................................................................... S6

Compound 2d......................................................................................................................................................... S8

Compound 2e ....................................................................................................................................................... S10

Compound 2f ....................................................................................................................................................... S12 13C NMR spectra of compounds 4,5 and 2a-f

Compound 4 ......................................................................................................................................................... S14

Compound 5 ......................................................................................................................................................... S15

Compound 2a ....................................................................................................................................................... S16

Compound 2b....................................................................................................................................................... S17

Compound 2c ....................................................................................................................................................... S18

Compound 2d....................................................................................................................................................... S19

Compound 2e ....................................................................................................................................................... S20

Compound 2f ....................................................................................................................................................... S21

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13C DEPT (CDCl3, 600 MHz) of compound 4.

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13C DEPT (CDCl3, 600 MHz) of compound 5.

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13C NMR (CDCl3, 400 MHz) of compound 2a.

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13C NMR (CDCl3, 400 MHz) of compound 2b

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13C NMR (DMSO-d6, 400 MHz) of compound 2c.

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13C NMR (DMSO-d6, 400 MHz) of compound 2d.

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13C NMR (DMSO-d6, 400 MHz) of compound 2e.

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13C NMR (CDCl3, 400 MHz) of compound 2f.