Tetrahydrofuran → 5-Bromo-1-(2-hydroxyethyl)pyrimidin-2(1H)-one

To two 50 mL polypropylene conical tubes with caps was added 5-bromo-1-(2-(tert-butyldimethylsilyloxy)ethyl)pyrimidin-2(1H)-one (4.0 g, 12 mmol) (2 g in each tube) in tetrahydrofuran (50 mL, 12 mmol, 25 mL in each tube). To the mixture at 25° C. was added HF pyridine complex (8.0 mL, 12 mmol) (4 mL in each tube). After stirring for 30 minutes the solution was filtered through a polypropylene frit and the filtercake was washed with THF. The white filtercake was then dried in vacuo to afford the title compound as a white solid (1.6 g, 60% yield). MS (ESI, pos. ion.) m/z: 219 (MH+). Calc'd exact mass for C6H7BrN2O2: 219. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.64 (q, J=5.3 Hz, 2 H), 3.89 (t, J=5.2 Hz, 2 H), 4.96 (t, J=5.5 Hz, 1 H), 8.39 (d, J=3.3 Hz, 1 H), 8.61 (d, J=3.3 Hz, 1 H).

1. additionTo the mixture at 25° C. was added HF pyridine complex (8.0 mL, 12 mmol) (4 mL in each tube)
2. filtrationwas filtered through a polypropylene frit
3. washthe filtercake was washed with THF
4. customThe white filtercake was then dried in vacuo

ORD record

ord-1b3b18b7ab1247c2a48d9b90ffb6c9c3

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08314087B2