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[00265] Example 102A. 3-Amino-5-methylpyridin-2-ol: To a solution of 5-methyl-3- nitropyridin-2-ol (50 mg, 0.32 mmol) in MeOH (5 mL) was added ammonium chloride (174 mg, 3.24 mmol) and zinc (106 mg, 1.62 mmol). The reaction mixture was colored and stirred at rt for 1 h. The suspension was removed by a filter and washed the filter with MeOH. The solvent was evaporated under reduced pressure. The crude product was triturated with a mixed solvent of MeOH and EtOAc (1 : 1). The suspension was filtered and the solvent was removed under reduced pressure to Example 1013A (16 mg, 0.13 mmol, 40percent yield). NMR (400 MHz, MeOD) δ ppm 2.03 (s, 3 H), 6.56 (s, 1 H), 6.63 (s, 1 H).
Reference：
[1] Patent: WO2014/22343, 2014, A1, . Location in patent: Paragraph 00265
[2] Journal of the American Chemical Society, 1950, vol. 72, p. 2806
[3] Journal of the American Chemical Society, 1957, vol. 79, p. 3552
[4] Patent: EP2471792, 2012, A1, . Location in patent: Page/Page column 43
With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 2h;Sealed tube;
In a sealed tube, a mixture of 2-hydroxy-5-methyl-3-nitropyridine (463 mg; 3.00 mmol), <strong>[78385-26-9]3-bromomethyl-3-methyloxetane</strong> (991 mg; 6.01 mmol) and K2C03 (1.25 g; 9.01 mmol) in DMF (6 mL) was stirred at 60C for 2h. The reaction mixture was cooled down to room temperature. The insoluble material was filtered off and thefiltrate was concentrated. The residue poured onto a mixture of water and brine, then extracted with EtOAc. The organic layer was decanted, washed with brine, dried over MgSO4, filtered and the solvent was evaporated to give 750 mg of crude product as a yellow oil. The crude was purified by chromatography over silica gel (irregular SiOH, 24 g; gradient: from 100% DCM to 98% DCM, 2% MeOH). The pure fractions werecollected and the solvent was evaporated to give intermediate 471 in 2 fractions: 287 mg of a yellow oil (40% yield) and 365 mg of a yellow solid (51% yield).
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