Pyridine → Phenyl (5-methylpyrazin-2-yl)carbamate
Reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5]([CH3:8])=[CH:4][N:3]=1.N1C=CC=CC=1.Cl[C:16]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17]>C(Cl)Cl>[C:19]1([O:18][C:16](=[O:17])[NH:1][C:2]2[CH:7]=[N:6][C:5]([CH3:8])=[CH:4][N:3]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-Amino-5-methylpyrazine (5.16 g, 47 mmol) was dissolved in CH2Cl2 (52 mL), stirred and cooled to 0° C. under N2. To this, pyridine (4.8 mL, 59 mmol) was added followed by phenyl chloroformate (6.2 mL, 59 mmol), dropwise, over 15 min, causing a precipitate to form. The mixture was stirred at 0° C. for 1 h. Then the reaction was quenched with 0.25 M HCl (40 mL) and anhydrous ether (50 mL), and stirred at 0° C., for 30 min. The precipitate was isolated by filtration, washed with DI H2O (20 mL) and ether (2×25 mL), and dried under vacuum to give the product (7.4 g) as a white fluffy powder.
Workup
- customto form
- stirringThe mixture was stirred at 0° C. for 1 h
- customThen the reaction was quenched with 0.25 M HCl (40 mL) and anhydrous ether (50 mL)
- stirringstirred at 0° C., for 30 min
- customThe precipitate was isolated by filtration
- washwashed with DI H2O (20 mL) and ether (2×25 mL)
- customdried under vacuum
Sources & evidence
- ORD record
- ord-2bc2e5cd578e412896d2a2ea59067622
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093244B2
Reaction notes
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