ETHYL PYRROLO[1,2-C]PYRIMIDINE-3-CARBOXYLATE

To a solution of 1H-pyrrole-2-carbaldehyde (9.51 g, 100.0 mmol, 1.0 eq) in DCM (150.0 mL) was added DBU (15.2 g, 100.0 mmol, 1.0 eq), followed by ethyl 2-isocyanoacetate (11.3 g, 100.0 mmol, 1.0 eq). The resulting mixture was heated to refluxed for 3 h, then 10percent AcOH (250 mL), and separated, the organic phase was washed with water (100 mL x 2), dried over anhydrous MgSO4, filtrated and concentrated. The residue was purified by column chromatography (PE/EA=4/1, vlv) to afford ethyl pyrrolo[1, 2-cjpyrimidine-3-carboxylate as a yellow solid (18.5 g, 97.3percent).[1114] A solution of pyrrole-2-carboxaldehyde (3.6 g, 38.1 mmol) in 40 mL dry THF is added to ethyl isocyanoacetate (4.3 g, 38.1 mmol) and DBU (5.8 g, 38.2 mmol) in 60 mL dry THF. After stirring at RT overnight, the reaction is neutralized with 10percent AcOH. The solvent is removed in vacuo. The residue is taken up in EtOAc/H2O, the aqueous layer is extracted with EtOAc, dried (MgSO4), filtered and concentrated. The residue is purified by flash chromatography on silica gel eluting with 30-70percent EtOAc/hexanes. The carboxylate is obtained (4.45 g, 61percent) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 8.86, 8.24, 7.54, 7.01, 6.78, 4.45, 1.44.

Molecular Weight:190.20
XLogP3:2.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:190.074227566
Monoisotopic Mass:190.074227566
Topological Polar Surface Area:43.6
Heavy Atom Count:14
Complexity:220
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes