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CAPLUS COPYRIGHT 2011 ACS
||Process for preparation of 5-alkyl-7H-pyrrolo[2,3-d]pyrimidin-4-ols
||Bednarz, Mark S.; Kanamarlapudi, Ramanaiah C.; Wu, Wenxue
||Lexicon Pharmaceuticals, Inc., USA
||U.S. Pat. Appl. Publ., 9 pp. CODEN: USXXCO
This invention pertains to processes for the preparation of 5-alkyl-7H-pyrrolo[2,3-d]pyrimidin-4-ols and salts, solvates thereof. For example, to a solution of cyano-acetamide in ethanol was added 21% sodium ethoxide solution in ethanol at room temperature. To the resulting mixture was added acetamidoacetone and the resulting mixture was then heated at 50 degrees C for 3.25 h to give 2-amino-4-methyl-1H-pyrrole-3-carboxamide. Without isolation, to the above pyrrole reaction mixture was added Et formate at 50 degrees C and the reaction mixture was heated about 3.5 h at 50 degrees C. The reaction mixture was concentrated under vacuum, dissolved in water at 40-45 degrees C, acidified to pH 5.6 using 6 N HCl, concentrated at 65-70 degrees C under vacuum to about 200 mL, and cooled slowly to room temperature to form a solid. The solid was filtered, washed with water, and dried at 55 degrees C under vacuum to give 5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ol as a red powder at 36% yield with 98.0% purity by HPLC.
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