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Synthesis of PreQ0 and chloro-intermediate 9. Reagents and conditions: (a) Methyl formate, NaOMe, PhMe, 3 h, 0 °C; (b) 2,6-diaminopyrimidin-4(3H)-one, NaOAc, H2O, 17 h, 100 °C, 60% (over two steps); (c) PivCl, pyridine, 2 h, 85 °C, 64%; (d) POCl3, DMA, BnEt3NCl, MeCN, 1 h, 90 °C, 35%.
