3-AMINO-5-BROMO-1-METHYLPYRIDIN-2(1H)-ONE
- Product Name
- 3-AMINO-5-BROMO-1-METHYLPYRIDIN-2(1H)-ONE
- CAS No.
- 910543-72-5
- Chemical Name
- 3-AMINO-5-BROMO-1-METHYLPYRIDIN-2(1H)-ONE
- Synonyms
- 3-Amino-5-bromo-1-methylp...;3-Amino-5-bromo-1-methylpyridin-2-one;3-amino-5-bromo-1-methyl-2-pyridinone;3-AMINO-5-BROMO-1-METHYLPYRIDIN-2(1H)-ONE;3-amino-5-bromo-1-methyl-2(1H)-Pyridinone;l-Methyl-3-aMino-5-broMo-l-H-pyridin-2-one;2(1H)-Pyridinone, 3-amino-5-bromo-1-methyl-;3-amino-5-bromo-1-methyl-1,2-dihydropyridin-2-on;3-amino-5-bromo-1-methyl-1,2-dihydropyridin-2-one
- CBNumber
- CB32451155
- Molecular Formula
- C6H7BrN2O
- Formula Weight
- 203.04
- MOL File
- 910543-72-5.mol
3-AMINO-5-BROMO-1-METHYLPYRIDIN-2(1H)-ONE Property
- Boiling point:
- 258.7±40.0 °C(Predicted)
- Density
- 1.713±0.06 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- pka
- 2?+-.0.20(Predicted)
- Appearance
- Light brown to brown Solid
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- A602183
- Product name
- 3-Amino-5-bromo-1-methylpyridin-2(1H)-one
- Packaging
- 100mg
- Price
- $75
- Updated
- 2021/12/16
- Product number
- 068584
- Product name
- 3-Amino-5-bromo-1-methylpyridin-2(1H)-one
- Purity
- >95%
- Packaging
- 1g
- Price
- $115
- Updated
- 2021/12/16
- Product number
- 4H56-9-43
- Product name
- 3-Amino-5-bromo-1-methylpyridin-2-one
- Packaging
- 1g
- Price
- $120
- Updated
- 2021/12/16
- Product number
- 2888AF
- Product name
- 3-Amino-5-bromo-1-methylpyridin-2(1H)-one
- Packaging
- 25g
- Price
- $531
- Updated
- 2021/12/16
- Product number
- 4H56-9-43
- Product name
- 3-Amino-5-bromo-1-methylpyridin-2-one
- Packaging
- 25g
- Price
- $698
- Updated
- 2021/12/16
3-AMINO-5-BROMO-1-METHYLPYRIDIN-2(1H)-ONE Chemical Properties,Usage,Production
Uses
3-Amino-5-bromo-1-methylpyridin-2(1H)-one is a useful reagent used in the preparation of novel 5-phenylpyridin-2(1H)-one derivatives as potent reversible Bruton''s tyrosine kinase inhibitors with antiarthritic activity for the treatment of Rheumatoid arthritis.
Synthesis
153888-45-0
910543-72-5
General procedure for the synthesis of 3-amino-5-bromo-1-methyl-3-nitropyridin-2(1H)-one from 5-bromo-1-methyl-3-nitropyridin-2(1H)-one: To a 1-liter three-necked round-bottomed flask fitted with a mechanical stirrer and a reflux condenser, under nitrogen protection, was added 5-bromo-1-methyl-3-nitropyridin-2(1H)-one (21.7 g, 93.3 mmol) , ethanol (305 mL), iron powder (-325 mesh, 52.1 g, 933 mmol) and 2N hydrochloric acid (50 mL, 100 mmol). The reaction mixture was heated and stirred at 60°C for 2 hours. After completion of the reaction, it was cooled to room temperature and the pH was adjusted to 8 (measured by pH paper) by adding potassium carbonate. The resulting suspension was filtered and the filter cake was washed with ethanol (4 x 100 mL). The filtrates were combined and concentrated under reduced pressure to give a brown solid. The solid was purified by silica gel column chromatography to afford the target product 3-amino-5-bromo-1-methylpyridin-2(1H)-one (14.5 g, 77% yield) as an off-white powder with a melting point of 104-105 °C. 1H NMR (500 MHz, DMSO-d6) δ 7.15 (d, 1H, J = 2.5 Hz), 6.46 (d, 1H, J = 2.5 Hz), 5.45 (bs, 2H), 3.40 (s, 3H); MS (ESI+) m/z 203 (M+H).
References
[1] Organic Process Research and Development, 2014, vol. 18, # 1, p. 228 - 238
[2] Patent: US2009/82330, 2009, A1. Location in patent: Page/Page column 39-41
[3] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 11, p. 3021 - 3029
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 2, p. 755 - 758
[5] Patent: WO2006/99268, 2006, A2. Location in patent: Page/Page column 69
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