Ammonia → 3,6-Dimethylpyrazin-2-amine
Reaction equation
[NH3:1].O.Cl[C:4]1[C:5]([CH3:11])=[N:6][CH:7]=[C:8]([CH3:10])[N:9]=1>>[CH3:11][C:5]1[C:4]([NH2:1])=[N:9][C:8]([CH3:10])=[CH:7][N:6]=1Participants
Conditions
- Temperature
- 165 °C
Procedure
Ammonia in water (3 mL, 48.5 mmol) was added to 3-chloro-2,5-dimethylpyrazine (0.121 mL, 1 mmol) and the mixture heated by microwaves to 165° C. for 7 hours. Following LCMS analysis, the reaction was then reheated to 165° C. for a further 16 hours, by microwaves. After cooling, the solvent was removed under a stream of nitrogen and the crude redissolved in dichloromethane (20 mL). Water (25 mL) was added and the mixture basified to pH14 using sodium hydroxide solution (18 N). The organic layer was removed and the aqueous layer extracted with dichloromethane (5×25 mL). The organic phases were combined and dried using a hydrophobic frit, then evaporated in vacuo to give the title product (109 mg). This was used directly in the next step with no further purification. LCMS (2 min, high pH) Rt 0.47 min, m/z (ES+) 124 (M+H).
Workup
- temperatureAfter cooling
- customthe solvent was removed under a stream of nitrogen
- dissolutionthe crude redissolved in dichloromethane (20 mL)
- additionWater (25 mL) was added
- customThe organic layer was removed
- extractionthe aqueous layer extracted with dichloromethane (5×25 mL)
- customdried
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-e1b1cbb5c1f7408f9300b617d7bfe351
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242972B2
Reaction notes
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