Yield:-

Reaction Conditions:

with triethylamine in tetrahydrofuran at 0 - 20;

Steps:

To a solution of 4,6-dichloro-5-nitro-pyrimidine (3.00 g, 15.5 mmol) in anhydrous THF (40 mL) was added dropwise a solution of 1,2,3,4-tetrahydroquinoline 10(2.07 g, 15.5 mmol) and triethylamine (3.3 mL, 23.3 mmol) in anhydrous THF (20 mL) in ice bath. After warmed to room temperature, the reaction mixture was stirred over night then concentrated in vacuo. The residue was dissoved in CH₂Cl₂ (50 mL) and washed with INHCl (30 mLx3), brine (30 mLx3), dried over anhydrous MgSO₄. Concentration in vacuo and EPO purification by flash chromatography on a silica gel column (Petroleum/ EtOAc 10:1, v/v) provided the desired product 3.46 g (77%), brown solid, mp 130-131 ⁰C. IH NMR (CDCl₃):δ8.06 (s, IH), 7.21 (d, J = 7.5 Hz, IH), 7.14 (td, J = 7.2 Hz, 1.5 Hz, IH), 7.07 (td, J = 8.1 Hz, 1.8 Hz, IH), 6.91 (dd, J = 7.5 Hz, 0.9 Hz, IH), 4.02 (t, J = 6.6 Hz, 2H), 2.79 (t, J = 6.6 Hz, 2H), 2.13-2.04 (m, 2 H); 13C NMR (CDC1₃):6157.1, 154.4, 153.2, 137.5, 132.6, 128.8, 126.4, 126.2, 119.3, 47.2, 26.3, 23.8; ES-MS: 291.0 [M+H] +.

References:

WO2006/89298,2006,A2 Location in patent:Page/Page column 101-102