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| | 4-Hydroxy-1-Methyl-1h-pyridin-2-one Basic information |
| Product Name: | 4-Hydroxy-1-Methyl-1h-pyridin-2-one | | Synonyms: | 4-Hydroxy-1-Methyl-1h-pyridin-2-one;4-Hydroxy-1-Methyl-2-pyridone;4-Hydroxy-1-methylpyridin-2(1H)-one;1,2-dihydro-4-hydroxy-1-methyl-2-oxopyridine;4-hydroxy-1-methylpyridin-2-one;4-hydroxy-1-methyl-1,2-dihydropyridin-2-one;2(1H)-Pyridinone, 4-hydroxy-1-methyl-;1-methyl-4-hydroxy-2-pyridineone | | CAS: | 40357-87-7 | | MF: | C6H7NO2 | | MW: | 125.13 | | EINECS: | | | Product Categories: | | | Mol File: | 40357-87-7.mol |  |
| | 4-Hydroxy-1-Methyl-1h-pyridin-2-one Chemical Properties |
| Melting point | 171-172 °C | | Boiling point | 266.6±40.0 °C(Predicted) | | density | 1.309±0.06 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | pka | 4.50±1.00(Predicted) | | Appearance | White to off-white Solid |
| | 4-Hydroxy-1-Methyl-1h-pyridin-2-one Usage And Synthesis |
| Uses | 4-Hydroxy-1-methyl-2-pyridone is a reactant used in the synthesis of 3-deaza-3-halouracil nucleosides with cytostatic activity in three cancer cell lines. | | Synthesis | General Steps:
Example 1 d-R2 group 3 preparation of 4-(benzyloxy)-1-methylpyridin-2(1H)-one: to a round-bottomed flask equipped with a condenser was added 4-(benzyloxy)pyridin-2(1H)-one (2.012 g, 10.0 mmol), K2CO3 (2.76 g, 20.0 mmol), MeI (2.129 g, 15.0 mmol) and MeOH (12.5 mL, 0.8 M) and then heated at 65 °C overnight. At this temperature, LCMS showed complete conversion to product. Post-treatment: the reaction mixture was filtered through diatomaceous earth. The filtrate was concentrated to an oil and left to solidify. The mass recovery was 1.95 g (91%). The substance could be used in the next step without further purification.
Preparation of 4-hydroxy-1-methylpyridin-2(1H)-one: To a round bottom flask was added 4-(benzyloxy)-1-methylpyridin-2(1H)-one (646 mg, 3.0 mmol), 10% Pd/C (160 mg), ammonium formate (568 mg, 9.0 mmol) and methanol (15 mL, 0.2 M). The resulting mixture was heated at 40 °C for 1 h, at which point the LCMS showed complete conversion to product. Post-treatment: the mixture was filtered through diatomaceous earth, concentrated and purified by preparative high performance liquid chromatography (PvPLC) to afford 1-methyl-4-hydroxy-2-pyridone as a colorless oil (215 mg, 57%). | | References | [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 17, p. 5243 - 5263
[2] Patent: WO2014/43272, 2014, A1. Location in patent: Paragraph 0260; 0262
[3] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 7, p. 871 - 874 |
| | 4-Hydroxy-1-Methyl-1h-pyridin-2-one Preparation Products And Raw materials |
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