反応 #53369

反応方程式

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

溶媒

THF

triethylamine

反応条件

後処理

1. 1
   温度at reflux temperature for 3 h
2. 2
   その他the supernatant was separated
3. 3
   その他the solvent was removed under reduced pressure
4. 4
   洗浄The 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
   ろ過the yellow solid was filtered off
8. 8
   その他dried
9. 9
   その他recrystallized twice from ethanol
10. 10
    その他to give 181 mg (41%) of V as yellow solid

実験手順

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]+.

出典