تفاعل #66837

معادلة التفاعل

5-tert-Butyl 3-ethyl 2-amino-6,7-dihydrothieno[3,2-c]pyridine-3,5(4H)-dicarboxylate

formamidine acetate

→

title compound

المردود 56.4%

tert-Butyl 4-oxo-3,4,7,8-tetrahydropyrido[3′,4′:4,5]thieno[2,3-d]pyrimidine-6(5H)-carboxylate

المردود 56.4%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent was then removed in vacuo
2. 2
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
3. 3
   غسيلThe organic layer was washed with water
4. 4
   تجفيفdried over sodium sulfate
5. 5
   أخرىthe solvent was removed in vacuo
6. 6
   أخرىThe residue was triturated with tert-butyl methyl ether
7. 7
   ترشيحthe precipitate was collected by suction filtration

الإجراء التجريبي

5-tert-Butyl 3-ethyl 2-amino-6,7-dihydrothieno[3,2-c]pyridine-3,5(4H)-dicarboxylate from Example 73A (780 mg, 2.39 mmol) was dissolved in DMF (8 mL), and formamidine acetate (373 mg, 3.58 mmol) was added. The reaction mixture was heated to 100° C. overnight. The solvent was then removed in vacuo, and the residue was dissolved in ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and the solvent was removed in vacuo. The residue was triturated with tert-butyl methyl ether, and the precipitate was collected by suction filtration to yield 414 mg (56%) of the title compound as a tan solid. The mother liquor was concentrated and purified by preparative HPLC to yield a second batch of 36 mg (5%).

المصدر