تفاعل #1586208

معادلة التفاعل

morpholine

7-methyl-1H-pyrido[3′,2′:4,5]furo[3,2-d]pyrimidine-2.4-dione

PCl5

POCl3

→

product

المردود 30.0%

2-Chloro-7-methyl-4-morpholin-4-yl-pyrido[3′,2′:4,5]furo[3,2-d]pyrimidine

المردود 30.0%

المذيبات

MeOH

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةOnce cooled down to rt
2. 2
   workup.ADDITIONthe mixture was poured dropwise very slowly
3. 3
   أخرىcrushed ice over 2 h
4. 4
   درجة الحرارةwarmed up to rt for 1 h
5. 5
   استخلاصThe resulting aqueous was extracted with EtOAc (3×100 mL) and CH2Cl2 (4×100 mL)
6. 6
   تجفيفThe combined organics were dried over MgSO4
7. 7
   أخرىthe solvent was removed in vacuo
8. 8
   workup.STIRRINGThe reaction mixture was stirred for 3 h
9. 9
   أخرىthe solvent was removed in vacuo
10. 10
    أخرىThe residue was further purified by silica gel column chromatography with hexane/EtOAc (1:1-0:1)

الإجراء التجريبي

To a mixture of 7-methyl-1H-pyrido[3′,2′:4,5]furo[3,2-d]pyrimidine-2.4-dione (1.6 g, 4.20 mmol, 1 eq) 17, and PCl5 (10.5 g, 50 mmol, 12 eq) was added at rt POCl3 (33.5 mL, 357 mmol, 85 eq) under Ar(g). The reaction mixture was refluxed at 115° C. overnight. Once cooled down to rt, the mixture was poured dropwise very slowly onto stirred crushed ice over 2 h, then warmed up to rt for 1 h. The resulting aqueous was extracted with EtOAc (3×100 mL) and CH2Cl2 (4×100 mL). The combined organics were dried over MgSO4 and the solvent was removed in vacuo. To this residue in dry MeOH (50 mL) was added at rt morpholine (0.92 mL, 10.5 mmol, 2.5 eq) under Ar(g). The reaction mixture was stirred for 3 h, then the solvent was removed in vacuo. The residue was further purified by silica gel column chromatography with hexane/EtOAc (1:1-0:1) to yield the product as a pale brown solid (384 mg, 30%).

المصدر