Sodium Iodide → 3-[5-[4-(2-Methoxyphenyl)piperazin-1-yl]pentyl]thieno[3,4-d]-pyrimidine-2,4-dione

Participants

Reaction Steps

The above urea (8.0 g, 23 mmol) was reacted with 1-(2-methoxyphenyl)piperazine hydrochloride (10.48 g, 45 mmol), NaI (1.72 g, 11 mmol) and NaHCO3 (7.69 g, 92 mmol) in 50 mL of 2-propanol at reflux for 6 hours under a nitrogen blanket. After cooling, water was added and the 2-propanol was removed by distillation. The brown residue was dissolved in CH2Cl2 and washed with water and brine and dried (MgSO4). After the solvent has been removed in vacuo, the tan residue was dissolved in MeOH and treated with 1.1 equivalents of 50% NaOH and the solution was refluxed for 3.5 hours. The pH of the solution was adjusted to 6 with 2N HCL and the methanol was removed by distillation. The resulting oil was dissolved in CH2Cl2 and washed with water and brine and dried (MgSO4). Solvent removal produced 10.81 g (91%) of 3-[5-[4-(2-methoxyphenyl)piperazin-1-yl]pentyl]thieno[3,4-d]pyrimidine-2,4-dione which was crystallized from CH2Cl2 /ether to afford a tan solid, mp 148°-153° C.

Provenance & Evidence