Water → N-Methyl-9-vinyl-9H-purin-6-amine
Reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]=[CH2:12].[CH3:13][NH2:14].O.Cl.CN>C1COCC1>[CH3:13][NH:14][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]=[CH2:12]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
6-Chloro-9-vinylpurine (JOC 1968, 33, 1341) (0.54 g, 3 mmol), was added to methylamine (˜15 mmol, 2.0M in THF) in THF (5 mL) and the mixture was stirred for 5 h at rt. Water was added to dissolve the white precipitate (methylamine hydrochloride). The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, concentrated on a rotavap, and then subjected to silica gel column chromatography (5% methanol/methylene chloride) yielding the desired product.
Workup
- extractionThe aqueous layer was extracted with ethyl acetate
- dry with materialthe combined organic layers were dried over sodium sulfate
- concentrationconcentrated on a rotavap
Sources & evidence
- ORD record
- ord-4900766008484c3097bf3fce12f42405
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08586566B2
Reaction notes
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