Реакция #1559

Уравнение реакции

trifluoroacetic anhydride

5-aminocarbonylmethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

Compound 275

5-aminocarbonylmethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

pyridine

→

6-ethyl-5-cyanomethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

Выход 49.8%

Растворители

ether

THF

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   Промывкаwashed with 20 mL of saturated aqueous NaHCO3
3. 3
   Сушкаdried over MgSO4
4. 4
   ДругоеRemoval of the solvent
5. 5
   workup.WAITleft 0.24 g of crude product as a yellow solid
6. 6
   ПромывкаFlash chromatography on 30 g of silica gel, eluting sequentially with 50, 75 and 100% ether in hexanes

Методика

A stirred suspension of 0.25 g (0.85 mmol) of 5-aminocarbonylmethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 275) in 12 mL of THF was cooled in an icebath and 0.15 mL (1.9 mmol) of pyridine was added followed by 0.13 mL (0.92 mmol) of trifluoroacetic anhydride. The mixture was stirred in the ice bath for 4 h, diluted with 80 mL of ether, washed with 20 mL of saturated aqueous NaHCO3 and dried over MgSO4. Removal of the solvent left 0.24 g of crude product as a yellow solid. Flash chromatography on 30 g of silica gel, eluting sequentially with 50, 75 and 100% ether in hexanes afforded 0.13 g of 6-ethyl-5-cyanomethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 277) as a white solid, m.p. 178°-180° C. 1 H-NMR (CDCl3) 1.3(3H,t), 2.4(1H,t), 2.75(2H,q), 3.75(2H,s), 4.6(2H,d), 7.55(3H,m), 7.7(2H,m).

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