Trimethyl orthoformate → HCID 59799574, compound

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Pale yellow solid. Synthesized from 2-(2-amino-5-fluorophenylamino)-6-chloro-9-(tetrahydro-2H-pyran-4-yl)-7H-purin-8(9H)-one (160 mg, 0.42 mmol) in anhydrous methanol (10 mL), using anhydrous trimethylorthoformate (1 mL) and methane sulfonic acid (5 drops) with stirring under Ar at room temperature for 2 h (HPLC monitoring). The solvent was removed in vacuo and the residue purified by column chromatography (silica gel, gradual elution with 2% methanol in methylene chloride to 10% methanol in methylene chloride) to afford the desired product (120 mg, 73% yield). 1H NMR (300 MHz, CDCl3+CD3OD) δ, ppm: 9.03 (s, 1H), 8.40-8.20 (m, 1H), 7.82-7.72 (m, 1H), 7.17-7.11 (m, 1H), 4.72-4.58 (m, 1H), 4.28-4.13 (m, 2H), 3.70-3.62 (m, 2H), 2.90-2.72 (m, 2H), 1.90-1.78 (m, 2H); MS (EI) m/z 389.2 (MH)+.

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