تفاعل #995305

معادلة التفاعل

HCl

methyl {5-[4-(2-bromo-2-methylpropanoyl)phenyl]bicyclo[3.2.2]non-1-yl}acetate

Intermediate 24

methyl {5-[4-(2-bromo-2-methylpropanoyl)phenyl]bicyclo[3.2.2]non-1-yl}acetate

5,6-diaminopyrimidin-4-ol

→

title compound

المردود 65.0%

Methyl {5-[4-(4-amino-7,7-dimethyl-7H-pyrimido[4,5-b][1,4]oxazin-6-yl)phenyl]bicyclo[3.2.2]non-1-yl}acetate

المردود 65.0%

المذيبات

EtOH

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe suspension was heated
2. 2
   درجة الحرارةto cool
3. 3
   أخرىthe solvent removed
4. 4
   workup.ADDITIONthe residue treated with 2M NaOH (2 mL)
5. 5
   استخلاصThe aqueous phase was extracted into EtOAc (3×50 mL)
6. 6
   تجفيفdried (MgSO4)
7. 7
   تركيزconcentrated
8. 8
   أخرىto leave a pale yellow gum
9. 9
   أخرىThis was purified on a 12 g Crawford silicycle cartridge, loading in DCM
10. 10
    غسيلeluting with 0-5-10% MeOH-DCM

الإجراء التجريبي

To a solution of methyl {5-[4-(2-bromo-2-methylpropanoyl)phenyl]bicyclo[3.2.2]non-1-yl}acetate (Intermediate 24; 80 mg, 0.19 mmol) in absolute EtOH (20 mL) was added 5,6-diaminopyrimidin-4-ol (30 mg, 0.21 mmol) followed by 1M HCl (0.21 mL). The suspension was heated under gentle reflux (80° C.) overnight then allowed to cool, the solvent removed and the residue treated with 2M NaOH (2 mL). The aqueous phase was extracted into EtOAc (3×50 mL), the organic extracts were combined, dried (MgSO4) and concentrated to leave a pale yellow gum. This was purified on a 12 g Crawford silicycle cartridge, loading in DCM and eluting with 0-5-10% MeOH-DCM, giving the title compound as a pale yellow gum (55 mg, 0.123 mmol, 65%); 1H NMR (CDCl3) 1.41-1.61 (14H, m), 1.71 (6H, s), 2.07 (2H, s), 3.61 (3H, s), 7.11 (2H, d), 7.51 (2H, d), 8.14 (1H, s); MS m/e MH+ 449.

المصدر