A Two Step Synthesis of the Nucleoside Q Precursor 2-Amino-5-cyanopyrrolo[2,3-d]pyrimidin 4-one (PreQ_o)

Michael T. Migawa Department of Chemistry, College of Literature, Science, and Arts, Ann Arbor, Michigan, 48109-1065; Department of Medicinal Chemistry, College of Pharmacy; The University of Michigan, Ann Arbor, Michigan, 48109-1065

Jack M. Hinkley Department of Chemistry, College of Literature, Science, and Arts, Ann Arbor, Michigan, 48109-1065; Department of Medicinal Chemistry, College of Pharmacy; The University of Michigan, Ann Arbor, Michigan, 48109-1065

Geoffrey C. Hoops Department of Chemistry, College of Literature, Science, and Arts, Ann Arbor, Michigan, 48109-1065; Department of Medicinal Chemistry, College of Pharmacy; The University of Michigan, Ann Arbor, Michigan, 48109-1065

Leroy B. Townsend Department of Chemistry, College of Literature, Science, and Arts, Ann Arbor, Michigan, 48109-1065; Department of Medicinal Chemistry, College of Pharmacy; The University of Michigan, Ann Arbor, Michigan, 48109-1065

Abstract

PreQ_o (1) is prepared in a 70 % yield by the condensation of chloro(formyl)acetonitrile (2) with 2,6-diaminopyrimidin-4-one (3), and subsequently converted to its amide derivative 5. Isolation of the intermediate 4 in the condensation reaction was also observed giving further insight into the proposed mechanism.

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A Two Step Synthesis of the Nucleoside Q Precursor 2-Amino-5-cyanopyrrolo[2,3-d]pyrimidin 4-one (PreQ_o)

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A Two Step Synthesis of the Nucleoside Q Precursor 2-Amino-5-cyanopyrrolo[2,3-d]pyrimidin 4-one (PreQo)

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A Two Step Synthesis of the Nucleoside Q Precursor 2-Amino-5-cyanopyrrolo[2,3-d]pyrimidin 4-one (PreQ_o)