Formamide → HCID 69560135, compound

A mixture of 2-amino-4-trifluoromethylpyrimidine (2.0 g, 12.2 mmol) and N,N-dimethylformamide dimethyl acetal (1.79 ml, 13.5 mmol) in toluene (50 ml) was heated at reflux for 1 h and then concentrated under reduced pressure. The resulting formamide was treated with ethyl bromoacetate (1.49 ml, 13.4 mmol) in toluene (60 ml) at reflux for 12 h and then concentrated under reduced pressure. The product was treated with saturated sodium hydrogencarbonate solution (50 ml) and extracted with EtOAc (3×50 ml). The combined organic extracts were washed with brine (50 ml), dried (MgSO4) and then concentrated while dry loading onto silica. Subsequent purification by column chromatography on silica using diethyl ether gave ethyl 7-trifluoromethylimidazo[1,2-α]pyrimidine-3-carboxylate (2.01 g, 64%): δH (360 MHz, CDCl3) δ 1.45 (3H, t, J 7.1), 4.47 (2H, q, J 7.1), 7.44 (1H, d, J 7.1), 8.60 (1H, s), 9.77 (1H, d, J 7.1); m/z (ES+) 347 (M++H).

1. temperaturewas heated
2. temperatureat reflux for 1 h
3. concentrationconcentrated under reduced pressure
4. temperatureat reflux for 12 h
5. concentrationconcentrated under reduced pressure
6. additionThe product was treated with saturated sodium hydrogencarbonate solution (50 ml)
7. extractionextracted with EtOAc (3×50 ml)
8. washThe combined organic extracts were washed with brine (50 ml)
9. dry with materialdried (MgSO4)
10. concentrationconcentrated
11. customwhile dry loading onto silica
12. customSubsequent purification by column chromatography on silica

ORD record

ord-89025a75a508489cb254aaf2c1ef502b

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07030128B2