Acetic Acid → Methyl pyrimidine-5-carboximidate

To a stirred suspension of 5-cyanopyrimidine (5.0 g, 47 mmol) in methanol (50 mL) was added 25% by weight sodium methoxide in methanol (1.2 g, 23 mmol). The mixture was stirred at room temperature for 17 h under nitrogen atmosphere and then acetic acid (2.72 ml, 47 mmol) was added dropwise. The resulting mixture was stirred for 4 h and then evaporated under reduced pressure to remove methanol and yield a residue. The residue was dissolved in ether (150 mL) and the solids were removed by filtration. The filtrate was concentrated under reduced pressure to yield methylpyrimidine-5-carbimidate (4.9 g, 75% yield). The crude product was used without further purification. 1H NMR (400 MHz, DMSO-d6, δ): 3.83 (s, 3H); 9.18 (s, 2H); 9.30 (s, 1H); 9.54 (s, 1H). ES-MS: [M++1]=138.

1. stirringThe resulting mixture was stirred for 4 h
2. customevaporated under reduced pressure
3. customto remove methanol
4. customyield a residue
5. customthe solids were removed by filtration
6. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-3dd96a688f914b818012f6dea41e71d1

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575184B2