Water → 2-Methylpyrimidine-5-carbaldehyde

To a stirred slurry of acetamidine hydrochloride (19.4 g, 0.20 mol) and vinamidinium salt (48.91 g, 0.183 mol) in acetonitrile (240 mL) was added a solution of 40% wt. NaOH in water (27.4 g, 0.274 mol) over a 30 minutes period. After the addition was complete, the resulting reaction mixture was stirred at room temperature overnight. The mixture was concentrated in vacuo and diluted with water (250 mL) and extracted with EtOAc (3×250 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography (0-100% EtOAc/hexanes) to afford a white solid.

1. additionAfter the addition
2. customthe resulting reaction mixture
3. concentrationThe mixture was concentrated in vacuo
4. additiondiluted with water (250 mL)
5. extractionextracted with EtOAc (3×250 mL)
6. dry with materialThe combined organic layers were dried over sodium sulfate
7. concentrationconcentrated in vacuo
8. customThe residue was purified by silica gel chromatography (0-100% EtOAc/hexanes)
9. customto afford a white solid

ORD record

ord-79f8da4c72524c5b974fbac6a46a4b0b

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653091B2