تفاعل #607481

معادلة التفاعل

103c

[4-(5-amino-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-3-yl]methyl acetate

LiOH

→

103d

المردود 36.0%

10-[4-(5-amino-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-(hydroxymethyl)-pyridin-2-yl]-4,4-dimethyl-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-9-one

المردود 36.0%

المذيبات

iPrOH THF

H2O

ظروف التفاعل

المعالجة

1. 1
   أخرىThe mixture was evaporated in vacuo
2. 2
   أخرىThe residue was partitioned between EtOAc and water
3. 3
   استخلاصThe combined EtOAc extract
4. 4
   تركيزwas concentrated under reduced pressure
5. 5
   أخرىthe residue was purified by silica-gel column chromatography
6. 6
   غسيلeluting with 10:1 dichloromethane/methanol

الإجراء التجريبي

A mixture of 103c (1.1 g, 2.3 mmol) and LiOH (450 mg, 11.0 mmol) in iPrOH/THF (1:1, 10 mL) and H2O (2.5 mL) was stirred at 40° C. for 0.5 h. The mixture was evaporated in vacuo. The residue was partitioned between EtOAc and water. The combined EtOAc extract was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 10:1 dichloromethane/methanol to afford 103d (350 mg, 36%) as a pale yellow solid. MS-ESI: [M+H]+ 434.3. 1H NMR (500 MHz, CDCl3) δ 8.44 (d, J=5.0 Hz, 1H), 7.59 (d, J=2.0 Hz, 1H), 7.21 (d, J=5.0 Hz, 1H), 6.83 (s, 1H), 6.82 (d, J=2.0 Hz, 1H), 5.04-5.03 (m, 1H), 4.63-4.62 (m, 1H), 4.50-4.48 (m, 1H), 4.30-4.28 (m, 1H), 4.16-4.10 (m, 3H), 3.87-3.85 (m, 1H), 3.65 (s, 3H), 2.57-2.56 (m, 2H), 2.50 (s, 2H), 1.26 (s, 6H).

المصدر