تفاعل #11927

معادلة التفاعل

4-chloro-2-phenyl-pyrido[2,3-d]pyrimidine

3-amino-5-methyl pyrazole

→

solid

المردود 50.7%

(5-Methyl-2H-pyrazol-3-yl)-(2-phenyl-pyrido[2,3-d]pyrimidin-4-yl)-amine

المردود 50.7%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was cooled to room temperature
2. 2
   ترشيحthe resulting suspension was filtered
3. 3
   غسيلwashed with Et2O
4. 4
   workup.DISSOLUTIONThe solid was dissolved in a mixture EtOH
5. 5
   استخلاصThe aqueous was extracted twice with ethyl acetate
6. 6
   تجفيفthe combined organic layers were dried (MgSO4)
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated in vacuo
9. 9
   أخرىThe residue was purified by flash chromatography (SiO2, DCM-MeOH gradient)

الإجراء التجريبي

To a solution of 4-chloro-2-phenyl-pyrido[2,3-d]pyrimidine (J. Pharm. Belg., 29, 1974, 145–148) (109 mg, 0.45 mmol) in THF (15 mL) was added 3-amino-5-methyl pyrazole (48 mg, 0.5 mmol) and the resulting mixture heated at 65° C. overnight. The mixture was cooled to room temperature and the resulting suspension was filtered and washed with Et2O. The solid was dissolved in a mixture EtOH:water and the pH adjusted to pH 7. The aqueous was extracted twice with ethyl acetate and the combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, DCM-MeOH gradient) to afford IV-31 as an off-white solid (69 mg, 50%): mp 234° C.; 1H NMR (DMSO) δ 2.14 (3H, s), 5.99 (1H, s), 7.20–7.40 (3H, m), 7.40–7.50 (3H, m), 8.60 (1H, d), 8.79 (1H, d), 12.82 (1H, br s); IR (solid) 2957, 2921, 2857, 1644, 1560, 1459, 1427; MS 303.2 (M+H)+.

المصدر