2-HYDROXY-3-AMINO-5-PICOLINE

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).[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).In a 10 mL reaction tube, a PTFE magnet is placed in a nitrogen atmosphere.Add 0.3 mmol of [00266] Example 102: To a suspension of (42 mg, 0.081 mmol) in sodium hydroxide (806 mu, 0.806 mmol) was added Example 102A (10 mg, 0.081 mmol). The reaction mixture was stirred at 40 C for over the weekend. The reaction was quenched with 1 N HC1 and MeOH. The organic layer was reduced in vacuo, and was purified using a 10 minutes gradient from 0 to 100%> B (Column: PHENOMENEX Axia Luna 100x20 mm 5u (10 min gradient). Solvent A: 10% ACN-90% H2O-0.1% TFA, Solvent B: 90% ACN-10% H2O-0.1% TFA) to give Example 102 (19 mg, 32% yield). lH NMR (400 MHz, MeOD) delta ppm 1.55 (s, 3H), 1.56 (s, 3H), 2.50 (s, 3 H), 3.25 - 3.27 (m, 1 H), 3.88 (d, J = 9.85 Hz, 1 H), 6.78 (d, J = 8.34 Hz, 1 H), 6.96 - 6.99 (m, 2 H), 7.09 - 7.13 (m, 1 H), 7.17 (d, J = 9.09 Hz, 2 H), 7.50 - 7.55 (m, 3 H), 7.93 (d, J = 8.08 Hz, 1 H), 7.98 (m, 1 H), 8.16 (m, 1 H). LCMS (ESI) m/z 590.0 (M+H)+, RT = 4.26 min (Method C).

Molecular Weight:124.14
XLogP3:-0.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:124.063662883
Monoisotopic Mass:124.063662883
Topological Polar Surface Area:55.1
Heavy Atom Count:9
Complexity:203
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes