Reaction #79055

Reaction equation

4-methylthiopyrido[4,3-d]pyrimidine

aniline

→

4-anilinopyrido-(4,3-d]pyrimidine

Yield 16.0%

Solvents

EtOH

Conditions

Workup

1. 1
   Temperatureis refluxed under N2 for 12 h
2. 2
   Filtrationis filtered

Procedure

A mixture of 4-methylthiopyrido[4,3-d]pyrimidine (174 mg, 0.97 mmol), and aniline (186.2 mg, 1.99 mmol) in EtOH (2 mL) is refluxed under N2 for 12 h. Cooling to 0° C. forms a solid which is filtered to yield 4-anilinopyrido-(4,3-d]pyrimidine (34.5 mg, 16%). 1H NMR (DMSO) δ 10.29 (1H, brs), 9.86 (1H, s), 8.82 (1H, d, J=5.8 Hz), 8.72 (1H, s), 7.85 (2H, d, J=7.5 Hz), 7.66 (1H, d, J=5.5 Hz), 7.45 (2H, t, J=8.0 Hz), 7.23 (1H, t, J=7.3 Hz).

Source