2-Amino-3-methoxy-5-methylpyrazine synthesis
- Product Name:2-Amino-3-methoxy-5-methylpyrazine
- CAS Number:89464-87-9
- Molecular formula:C6H9N3O
- Molecular Weight:139.16
74290-65-6
89464-87-9
(i) 2-Amino-3-bromo-5-methylpyrazine (0.374 g) was added to a freshly prepared methanolic solution of sodium methanolate (prepared by reacting sodium metal (0.115 g) with methanol (6 mL)). The reaction mixture was heated and refluxed for 18 h. Subsequently, it was cooled to room temperature and the solvent was removed by distillation under reduced pressure. Water (5 mL) was added to the residue and extracted with dichloromethane (3 x 20 mL). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane as eluent to afford 2-amino-3-methoxy-5-methylpyrazine as a white crystalline solid (0.208 g, 75% yield) with a melting point of 205°C (literature value 67°-69°C). Mass spectrum (positive chemical ionization): m/z 140 ([M + H]+).
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89464-87-9
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Yield:89464-87-9 92%
Reaction Conditions:
at 30 - 100; for 6 h;Inert atmosphere;
Steps:
35.2
[00791] To a mixture of 3-bromo-5-methyl-pyrazin-2-amine (31 g, 164.87 mmol) in MeOH (150 mL) was added NaOMe (14 g, 263.79 mmol) in one portion at 30 °C under N2. The mixture was stirred at 100 °C for 6 hrs. The mixture was concentrated under reduced pressure and the resulting residue was dissolved in water (100 mL). The mixture was extracted with EtOAc and the combined organic layers were washed with brine (20 mL), dried with Na2S04, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography (to afford 3-methoxy-5-methyl-pyrazin-2-amine (21 g, 92% yield) as a white solid. 1H MR (400 MHz, CDCh-d) δ ppm 7.39 (s, 1H) 4.59 (br s, 2 H) 3.97 (s, 3 H) 2.29 (s, 3 H)
References:
WO2018/136265,2018,A1 Location in patent:Paragraph 00791
74290-65-6
118 suppliers
$25.00/100mg
89464-87-9
47 suppliers
$29.00/100mg
124-41-4
724 suppliers
$12.00/25g
74290-65-6
118 suppliers
$25.00/100mg
89464-87-9
47 suppliers
$29.00/100mg
5521-58-4
229 suppliers
$14.00/250mg
89464-87-9
47 suppliers
$29.00/100mg