Réaction #1556

Équation de réaction

water

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

Compound 105

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

lithium aluminum hydride

lithium aluminum hydride

→

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

Solvants

ether

THF

ether

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe mixture was stirred for 1 h at room temperature
2. 2
   workup.WAITto stand for 1 h
3. 3
   AutreThe layers were separated
4. 4
   Extractionthe aqueous layer was extracted with 100 mL of ethyl acetate
5. 5
   Lavagethe combined organic extracts were washed with 50 mL of 5% aqueous NaOH
6. 6
   Séchagedried over MgSO4
7. 7
   AutreRemoval of the solvent
8. 8
   workup.WAITleft 1.36 g of crude product as an amber syrup
9. 9
   LavageFlash chromatography on 30 g of silica gel, eluting sequentially with 20, 40, 60, 80 and 100% ethyl acetate in hexanes

Mode opératoire

A stirred solution of 1.35 g (4.4 mmol) of 6-ethyl-5-methoxycarbonylmethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 105) in 30 mL of THF was cooled in an ice bath and a slurry of 0.10 g (2.6 mmol) of lithium aluminum hydride in 10 mL of ether was added. The ice bath was allowed to melt and the reaction mixture was stirred at room temperature for 3 h. An additional 0.05 g (1.3 mmol) of lithium aluminum hydride was added. The mixture was stirred for 1 h at room temperature. The mixture was poured into 100 mL of water and 100 mL of ether and allowed to stand for 1 h. The layers were separated and the aqueous layer was extracted with 100 mL of ethyl acetate. the combined organic extracts were washed with 50 mL of 5% aqueous NaOH and dried over MgSO4. Removal of the solvent left 1.36 g of crude product as an amber syrup. Flash chromatography on 30 g of silica gel, eluting sequentially with 20, 40, 60, 80 and 100% ethyl acetate in hexanes afforded 6-ethyl-5-(2-hydroxyethyl)-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 274) as an oil. 1H-NMR (CDCl3) 1.2(3H,t), 2.35(1H,t), 2.65(2H,q), 2.90(2H,t), 3.85(2H,t), 4.55(2H,d), 7.5(3H,m), 7.7(2H,m).

Source