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Generated: January 18, 2018

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Title:Process for preparing an A.sub.2A-adenosine receptor agonist and its polymorphs
Abstract: Synthesis methods suitable for large scale manufacture of the A.sub.2A-adenosine receptor agonist (1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminop- urin-2-yl}pyrazol-4-yl)-N-methylcarboxamide and precursors thereof.
Inventor(s): Zablocki; Jeff (Mountain View, CA), Elzein; Elfatih (Fremont, CA)
Assignee: Gilead Palo Alto, Inc. (Foster City, CA)
Filing Date:May 17, 2007
Application Number:11/750,295
Claims:1. A method of synthesizing (1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminop- urin-2-yl}pyrazol-4-yl)-N-methylcarboxamide ##STR00025## by contacting a compound of the formula (4): ##STR00026## and wherein the reaction is with aqueous methylamine at a temperature of approximately 2.5-7.5.degree. C. conducted in a sealed pressure reactor.

2. The method of claim 1, further comprising wherein the product is isolated by (a) degassing under vacuum at not more than 35.degree. C. to remove excess methylamine, (b) releasing the vacuum and cooling to 0-5.degree. C. for approximately 15-minutes to an hour, (c) filtering the slurry thus formed, (d) washing the contents of the filter with water followed by ethanol, and (e) drying the solid that remains under vacuum at a temperature that does not exceed 40.degree. C.

3. The method of claim 2 further comprising wherein the (1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminop- urin-2-yl}pyrazol-4-yl)-N-methylcarboxamide end product is further purified by (i) dissolving the dried solid from step (e) of claim 2 in a solvent, (ii) filtering any solid impurities from the solution, (iii) rinsing with additional solvent, (iv) adding solution to purified water that is maintained at approximately 78-88.degree. thereby forming a slurry, (v) stirring the slurry, (vi) cooling the slurry, (vii) filtering, (viii) washing the contents of the filter with water followed by ethanol, and (ix) drying the solid that remains under vacuum at a temperature that does not exceed 40.degree. C.

4. The method of claim 3, further comprising wherein the solvent of steps (i) and (iii) is dimethylsulfoxide.

5. The method of claim 4, further comprising wherein the residual water content in the final product is not more than 5.5% and the residual ethanol is not more that 2000 ppm.
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