Sodium Iodide → (E)-5-(2-Bromovinyl)uracil

To a solution of E-5-(2-bromovinyl)-2,4-dimethoxypyrimidine (2.45 g; 10 mmol) in AcOH (10 ml) was added NaI (3.3 g; 2.2 eq.; 22 mmol) and the solution heated under reflux for 3 h. The hot mixture was filtered and diluted with water (15 ml). After cooling, the precipitated product was filtered off, washed with acetone (50 ml) and ether (20 ml) and dried to give a pale yellow powder (1.40 g, 65%). Mp>320° C.; 60 MHz 1H-NMR, DMSO-6d, δ:7.60 (s, 1H, H-6); 7.30 (d, 1H, J=13 Hz, vinyl H); 6.80 (d, 1H, J=13 Hz, vinyl H).

1. temperaturethe solution heated
2. temperatureunder reflux for 3 h
3. filtrationThe hot mixture was filtered
4. additiondiluted with water (15 ml)
5. temperatureAfter cooling
6. filtrationthe precipitated product was filtered off
7. washwashed with acetone (50 ml) and ether (20 ml)
8. customdried

ORD record

ord-27e605a245bb4f7b80bf211c3a0f8864

Source dataset

uspto-grants-1994_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05356882