Methyl iodide → 2-[methyl-N-(methoxycarbonyl)amino]-6-(phenylthio)imidazo[1,2-a]pyridine
Reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][N:9]2[CH:21]=1)=[O:4].O1CCC[CH2:23]1.C([Li])CCC.CI>CCCCCC>[CH3:23][N:5]([C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:10][N:9]2[CH:21]=1)[C:3]([O:2][CH3:1])=[O:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A suspension of 1.0 g. (0.0033 moles) of 2-(methoxycarbonylamino)-6-(phenylthio)imidazo [1,2-a] pyridine in 35 ml. of tetrahydrofuran under a argon atmosphere is treated dropwise with 1.35 ml. of a 2.45 molar solution of butyllithium in hexane at -20° C. The resultant solution is stirred for 5 minutes and 0.469 g. (0.0033 moles) of methyliodide is added. The reaction mixture is allowed to warm to room temperature and stirred for 30 minutes. The solution is diluted with ice water and the solids are collected by filtration, washed with water and dried. The solid materials is chromatographed on silica gel and eluted with 1:99 methanol in methylene chloride affording 2-[methyl-N-(methoxycarbonyl)amino]-6-(phenylthio)imidazo [1,2-a] pyridine m.p. 147°-149° C.
Workup
- additionA suspension of 1.0 g
- customat -20° C
- filtrationthe solids are collected by filtration
- washwashed with water
- customdried
- customThe solid materials is chromatographed on silica gel
- washeluted with 1:99 methanol in methylene chloride
Sources & evidence
- ORD record
- ord-4d21daa091744738bb448cc666717126
- Source dataset
- uspto-grants-1980_12
- Patent number
- US04237300
Reaction notes
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