Methanol → 4,6-Diamino-2-methoxypyridine-3-carbonitrile
Reaction equation
[Na].Br[C:3]1[N:10]=[C:9]([NH2:11])[CH:8]=[C:7]([NH2:12])[C:4]=1[C:5]#[N:6].[CH3:13][OH:14]>>[NH2:12][C:7]1[C:4]([C:5]#[N:6])=[C:3]([O:14][CH3:13])[N:10]=[C:9]([NH2:11])[CH:8]=1Participants
Conditions
- Temperature
- 150 °C
Procedure
A heavy walled, sealable tube suitable for microwave heating was charged with 3 mL of methanol and 40 mg (1.7 mmol) of sodium. The mixture was stirred until all of the sodium had reacted, then 212 mg (1.00 mmol) of 2-bromo-4,6-diaminonicotinonitrile was added. The tube was sealed, and the mixture was heated with a microwave apparatus at 150° C. for 10 minutes then cooled and concentrated under reduced pressure. The residue was suspended in 10 mL of water, and extracted with ethyl acetate (1×20 mL, then 2×10 mL). The combined ethyl acetate layers were back extracted with brine (1×10 mL), dried over MgSO4, filtered, and concentrated to a solid. This was purified via silica gel chromatography, eluting with 60:40 hexanes:ethyl acetate to provide 114 mg (70%) of a white solid.
Workup
- temperatureA heavy walled, sealable tube suitable for microwave heating
- customhad reacted
- customThe tube was sealed
- temperaturethen cooled
- concentrationconcentrated under reduced pressure
- extractionextracted with ethyl acetate (1×20 mL
- extractionThe combined ethyl acetate layers were back extracted with brine (1×10 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated to a solid
- customThis was purified via silica gel chromatography
- washeluting with 60:40 hexanes
Sources & evidence
- ORD record
- ord-506fd542f32e49349d076a8016d3fe72
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07888374B2
Reaction notes
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