Water → 7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-6-(methoxymethyl)-1,8-naphthyridine
Reaction equation
[CH3:1][O:2][CH:3]([O:16][CH3:17])[C:4]1[C:13]([CH2:14][OH:15])=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][NH:7][C:6]=2[N:5]=1.[H-].[Na+].O.[CH2:21]1COCC1>>[CH3:17][O:16][CH:3]([O:2][CH3:1])[C:4]1[N:5]=[C:6]2[C:11]([CH2:10][CH2:9][CH2:8][NH:7]2)=[CH:12][C:13]=1[CH2:14][O:15][CH3:21]Participants
5
Procedure
To a solution of (2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methanol (intermediate 40, 94 mg, 0.394 mmol) in THF (2 ml) was added NaH (60% dispersion in mineral oil, 16.6 mg, 0.414 mmol). The resulting suspension was stirred at room temperature for 15 min, then Mel (0.026 ml, 0.414 mmol) was added and the reaction mixture was stirred for 28 h. The reaction mixture was poured into water and extracted with DCM (2×). The organic phase was then dried over Na2SO4, filtered and evaporated. The crude material was purified by normal phase chromatography (12 g silica gel cartridge, DCM/(DCM/MeOH 9/1) 100:0 to 50:50) to give the title compound as a yellow oil. (UPLC-MS 3) tR 0.51 min; ESI-MS 253.2 [M+H]+.
Workup
- additionMel (0.026 ml, 0.414 mmol) was added
- stirringthe reaction mixture was stirred for 28 h
- extractionextracted with DCM (2×)
- dry with materialThe organic phase was then dried over Na2SO4
- filtrationfiltered
- customevaporated
- customThe crude material was purified by normal phase chromatography (12 g silica gel cartridge, DCM/(DCM/MeOH 9/1) 100:0 to 50:50)
Sources & evidence
- ORD record
- ord-7d15c25766be41949af1e0813e03ad66
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266883B2
Reaction notes
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