2-Amino-3-bromo-5-methylpyrazine synthesis
- Product Name:2-Amino-3-bromo-5-methylpyrazine
- CAS Number:74290-65-6
- Molecular formula:C5H6BrN3
- Molecular Weight:188.03
5521-58-4
74290-65-6
General procedure for the synthesis of 2-amino-3-bromo-5-methylpyrazine from 2-amino-5-methylpyrazine: Bromine (8.80 g, 55.0 mmol) was slowly added to a solution of dichloromethane (250 mL) containing 5-methylpyrazin-2-amine (5.00 g, 45.8 mmol) and pyridine (4.35 g, 55.0 mmol). The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, water (150 mL) was added to the mixture for extraction and the organic layer was separated. The organic layer was washed with saturated brine (100 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum to afford the target compound 2-amino-3-bromo-5-methylpyrazine as a yellow solid (7.64 g, 88% yield). Mass spectrum (ESI, positive ion mode) m/z: 190.2 [M + H]+; 1H NMR (400 MHz, CDCl3) δ (ppm): 7.83 (s, 1H), 4.93 (s, 2H), 2.41 (s, 3H).
5521-58-4
226 suppliers
$14.00/250mg
74290-65-6
117 suppliers
$25.00/100mg
Yield:74290-65-6 88%
Reaction Conditions:
with pyridine;bromine in dichloromethane at 20;
Steps:
43.1 Step 1: 3-bromo-5-methylpyrazine-2-amine
To a solution of 5-methylpyrazin-2-amine (5.00g, 45.8 mmol) and pyridine (4.35g,55.0 mmol) in DCM (250 mL) was added bromine (8.80 g, 55.0 mmol). The mixture was stirredat rt overnight. To the reaction mixture was added water (150 mL), and the resulting mixture waspartitioned. The organic layer was washed with saturated brine (100 mL), dried over anhydroussodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound asa yellow solid (7.64 g, 88 %).MS (ESI, pos. ion) m/z: 190.2 [M+Ht;1H NMR (400 MHz, CDCh) 8 (ppm): 7.83 (s, lH), 4.93 (s, 2H), 2.41 (s, 3H).
References:
SUNSHINE LAKE PHARMA CO., LTD.;TANG, Changhua;REN, Qingyun;YIN, Junjun;YI, Kai;LEI, Yibo;WANG, Yejun;ZHANG, Yingjun WO2018/108125, 2018, A1 Location in patent:Paragraph 00511
5521-58-4
226 suppliers
$14.00/250mg
74290-65-6
117 suppliers
$25.00/100mg
74290-68-9
60 suppliers
$73.00/100mg