Pyrrolidine → 5-(Pyrrolidin-1-yl)pyrazin-2-amine
Reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5](Br)=[CH:4][N:3]=1.[NH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1>O>[NH2:1][C:2]1[CH:7]=[N:6][C:5]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][N:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 180 °C
Procedure
A solution of 0.6 g (3.45 mmol) of 2-amino-5-bromopyrazine and of 3 mL (36 mmol) of pyrrolidine, placed in a sealed tube, is heated in a microwave oven for two hours at 180° C. and 200 W. 100 mL of water is added to the reaction mixture and it is extracted three times with 50 mL of ethyl acetate. The organic phases are combined, washed three times with 20 mL of water and then once with 20 mL of a saturated aqueous solution of sodium chloride, dried over sodium sulfate and then concentrated at reduced pressure. The product obtained is then purified by chromatography on a silica column, eluting with a mixture of dichloromethane and methanol. We obtain 0.21 g of the expected compound in the form of a brown solid.
Workup
- extractionis extracted three times with 50 mL of ethyl acetate
- washwashed three times with 20 mL of water
- dry with materialonce with 20 mL of a saturated aqueous solution of sodium chloride, dried over sodium sulfate
- concentrationconcentrated at reduced pressure
- customThe product obtained
- customis then purified by chromatography on a silica column
- washeluting with a mixture of dichloromethane and methanol
Sources & evidence
- ORD record
- ord-e2e08e159d004a2bae2565f366d15d29
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716273B2
Reaction notes
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