Reacción #53369

Ecuación de reacción

3,5-Diamino-6-chloropyrazinoyl-2-methyl-pseudothiourea hydroiodide

4-(4-hydroxyphenyl)butylamine hydrobromide

4-(4-Hydroxyphenyl)butylamine hydrobromide

→

4-(4-Hydroxyphenyl)butylamidino-3,5-diamino-6-chloropyrazinecarboxamide hydrochloride

Disolventes

THF

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux temperature for 3 h
2. 2
   Otrothe supernatant was separated
3. 3
   Otrothe solvent was removed under reduced pressure
4. 4
   LavadoThe oily residue was washed with water (2×30 mL), ether (3×30 mL)
5. 5
   workup.ADDITION10% HCl (40 mL) was added
6. 6
   workup.STIRRINGThe mixture was vigorously stirred for 10 min
7. 7
   Filtraciónthe yellow solid was filtered off
8. 8
   Otrodried
9. 9
   Otrorecrystallized twice from ethanol
10. 10
    Otroto give 181 mg (41%) of V as yellow solid

Procedimiento

1-(3,5-Diamino-6-chloropyrazinoyl-2-methyl-pseudothiourea hydroiodide (0.4 g, 1.03 mmol) was added to a suspension of 4-(4-hydroxyphenyl)butylamine hydrobromide (IV) in a mixture of THF (35 mL) and triethylamine (3 mL). The reaction mixture was stirred at reflux temperature for 3 h, then the supernatant was separated and the solvent was removed under reduced pressure. The oily residue was washed with water (2×30 mL), ether (3×30 mL) and then 10% HCl (40 mL) was added. The mixture was vigorously stirred for 10 min then the yellow solid was filtered off, dried and recrystallized twice from ethanol to give 181 mg (41%) of V as yellow solid. Purity is 98% by HPLC, retention time is 9.77 min; 1H NMR (300 MHz, DMSO-d6) δ1.56 (br s, 4H), 2.48 (br s, 2H), 3.35 (m, 2H), 6.65 (d, J=8.5 Hz, 2H), 6.95 (d, J=8.6 Hz, 2H), 7.50 (br s, 2H), 8.75 (br s, 1H), 9.05 (br .s, 1H), 9.33 (br s, 2H), 10.55 (s, 1H); 13C NMR (75 MHz, CD3OD) 28.7, 29.8, 35.4, 42.4, 111.2, 116.1, 122.0, 130.0, 134.0, 155.0, 156.1, 156.8, 157.5, 167.0; APCI MS m/z=378 [C16H20ClN7O2+H]+.

Fuente