반응 #66708

반응 방정식

guanidine HCl

sodium methoxide

2-(4-Ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-3-phenylamino-acrylonitrile

guanidine HCl

sodium methoxide

→

5-(4-Ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-pyrimidine-2,4-diamine

수율 80.2%

용매

ethanol

EtOH

water

ethanol

반응 조건

후처리

1. 1
   온도the reaction mixture was heated
2. 2
   온도to reflux for 2 hours
3. 3
   온도The reaction mixture was cooled
4. 4
   추출extracted twice with EtOAc
5. 5
   세척washed with brine
6. 6
   건조dried over magnesium sulfate
7. 7
   기타Solvent was removed in vacuo

실험 절차

2-(4-Ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-3-phenylamino-acrylonitrile (360 mg, 1 mmol), guanidine HCl (411 mg, 4 mmol) and sodium methoxide (880 ul, 4 mmol, 4.9 M solution in methanol) in 5 mL absolute ethanol were heated to reflux in 5 ml absolute ethanol for 2 hours. Premixed guanidine HCl (411 mg, 4 mmol) and sodium methoxide (880 ul, 4 mmol, 4.9 M solution in methanol) in 1 ml EtOH was added via pipette, and the reaction mixture was heated to reflux for 2 hours. The reaction mixture was cooled, diluted with water, extracted twice with EtOAc, washed with brine, and dried over magnesium sulfate. Solvent was removed in vacuo to give 241 mg of 5-(4-Ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-pyrimidine-2,4-diamine as a white solid (74%). Mass Spec M+H=301, M.P.=181° C. Recrystallization of 175 mg of this product from MeOH and HO/diethyl ether afforded 98 mg of the corresponding HCl salt 49%, Mass Spec M+H=301, M.P.>300 C.

출처