تفاعل #309879

معادلة التفاعل

Sodium hydride

3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol

3-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol

5-bromo-2-(1-piperidinyl)pyrimidine

→

title compound

3-Cyclobutyl-7-{[2-(1-piperidinyl)-5-pyrimidinyl]oxy}-2,3,4,5-tetrahydro-1H-3-benzazepine

المذيبات

pyridine

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction mixture heated
2. 2
   درجة الحرارةat reflux for 2 hours
3. 3
   درجة الحرارةto cool
4. 4
   ترشيحfiltered
5. 5
   تركيزthe filtrate was concentrated in vacuo
6. 6
   workup.DISSOLUTIONThe crude residue was dissolved with ethyl acetate
7. 7
   غسيلwashed with water and brine
8. 8
   تجفيفThe organic layer was dried (magnesium sulfate)
9. 9
   ترشيحfiltered
10. 10
    تركيزconcentrated in vacuo
11. 11
    أخرىPurification of the resulting residue by column chromatography
12. 12
    غسيلeluting with a mixture of 0.880 ammonia:ethanol:dichloromethane (0.25:2.25:97.5 to 1:9:90)

الإجراء التجريبي

Sodium hydride (60% disp. in mineral oil, 44 mg, 1.1 mmol) was added to a stirred solution of 3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol (E3) (200 mg, 0.92 mmol) and copper (I) bromide (184 mg, 1.3 mmol) in pyridine (10 ml) at 0° C. After stirring for 0.5 hour at room temperature, 5-bromo-2-(1-piperidinyl)pyrimidine (D32) (0.669 g, 2.8 mmol) was added and the reaction mixture heated at reflux for 2 hours. The reaction was allowed to cool, filtered and the filtrate was concentrated in vacuo. The crude residue was dissolved with ethyl acetate and washed with water and brine. The organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Purification of the resulting residue by column chromatography eluting with a mixture of 0.880 ammonia:ethanol:dichloromethane (0.25:2.25:97.5 to 1:9:90) afforded the title compound (E140). MS (ES+) m/e 379 [M+H]+.

المصدر