تفاعل #2075735

معادلة التفاعل

2-(4-Chloro-2-fluoro-3-methoxyphenyl)-6-methoxy-7-methyl-7H-purine

thionyl chloride

sodium hydroxide

DMF

sodium hydroxide

HCl

→

title compound

المردود 49.3%

6-Chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)-7-methyl-7H-purine

المردود 49.3%

المذيبات

ethyl acetate

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةheated
2. 2
   درجة الحرارةat reflux for 2 h
3. 3
   درجة الحرارةAfter cooling
4. 4
   ترشيحThe precipitated material was collected by filtration
5. 5
   غسيلwashed with water
6. 6
   أخرىdried under vacuum at 80° C
7. 7
   درجة الحرارةThe mixture was heated
8. 8
   درجة الحرارةat reflux for 3 h
9. 9
   درجة الحرارةcooled
10. 10
    غسيلwashed twice with water, once with brine
11. 11
    أخرىdried
12. 12
    أخرىevaporated

الإجراء التجريبي

2-(4-Chloro-2-fluoro-3-methoxyphenyl)-6-methoxy-7-methyl-7H-purine (1.0 g, 3.1 mmol) was combined with 10 mL 6M HCl and heated at reflux for 2 h. After cooling, the mixture was diluted with 15 mL water and the pH was adjusted to 2 by addition of 2M aqueous sodium hydroxide. The precipitated material was collected by filtration, washed with water and dried under vacuum at 80° C. A 500 mg sample of the crude intermediate was slurried in chloroform (10 mL), treated with DMF (0.62 mL, 580 mg, 8.0 mmol) and then with thionyl chloride (0.58 mL, 950 mg, 8.0 mmol). The mixture was heated at reflux for 3 h, cooled and poured into 20 mL of ice-water. The pH was adjusted to 10 by addition of 1M sodium hydroxide. The precipitated product was taken up in ethyl acetate, washed twice with water, once with brine, dried and evaporated to give the title compound (500 mg, 49% yield over two steps): mp 184-186° C.: 1H NMR (DMSO-d6) δ 8.8 (s, 1H), 7.8 (dd, 1H), 7.46 (dd, 1H), 4.11 (s, 3H), 3.96 (s, 3H).

المصدر