Reacción #11925

Ecuación de reacción

Potassium carbonate

(5-cyclopropyl-1H-pyrazol-3-yl)-(2-chloro-quinazolin-4-yl)-amine

4-methylpiperidine

→

solid

Rendimiento 86.1%

(5-Cyclopropyl-2H-pyrazol-3-yl)-[2-(4-methylpiperidin-1-yl)-quinazolin-4-yl]-amine

Rendimiento 86.1%

Disolventes

tert-butanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture heated
2. 2
   Temperaturaat reflux overnight
3. 3
   ConcentraciónThe reaction mixture was concentrated in vacuo
4. 4
   workup.DISSOLUTIONthe residue dissolved in a mixture EtOH:water (1:3, 4 mL)
5. 5
   FiltraciónThe resulting suspension was filtered
6. 6
   Lavadowashed with water (×2)
7. 7
   Lavadorinsed with Et2O (×2)

Procedimiento

To a solution of (5-cyclopropyl-1H-pyrazol-3-yl)-(2-chloro-quinazolin-4-yl)-amine (118 mg, 0.41 mmol) in tert-butanol (3.0 mL) was added 4-methylpiperidine (0.49 mL, 4.1 mmol) and the reaction mixture heated at reflux overnight. The reaction mixture was concentrated in vacuo and the residue dissolved in a mixture EtOH:water (1:3, 4 mL). Potassium carbonate (57 mg, 0.41 mmol) was added and the mixture stirred at room temperature for 2 hours. The resulting suspension was filtered, washed with water (×2), and rinsed with Et2O (×2) to afford III-111 as a white solid (123 mg, 85%): mp 190° C.; 1H NMR (DMSO) δ 0.66 (2H, s), 0.93 (5H, br s), 1.07 (2H, d), 1.66 (3H, s), 1.91 (1H, s), 2.85 (2H, t), 4.72 (2H, d), 6.33 (1H, s), 7.06 (1H, t), 7.29 (1H, d), 7.52 (1H, t), 8.31 (1H, d), 9.95 (1H, s), 12.18 (1H, br s); IR (solid) 2925, 2852, 1622, 1590, 1581, 1558, 1494, 1481, 1453, 1435, 1394; MS 349.2 (M+H)+.

Fuente