Reaktion #53374

Reaktionsgleichung

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

4-(4-hydroxyphenyl)butylamine hydrobromide

4-(4-Hydroxyphenyl)butylamine hydrobromide

→

5

Ausbeute 84.4%

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

Ausbeute 84.4%

Lösungsmittel

THF

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe supernatant was separated
2. 2
   Sonstigethe solvent was removed under reduced pressure
3. 3
   WaschenThe oily residue was washed with water (2×30 mL), ether (3×30 mL)
4. 4
   workup.ADDITION10% HCl (40 mL) was added
5. 5
   workup.STIRRINGThe mixture was vigorously stirred for 10 min
6. 6
   Filtrationthe yellow solid was filtered off
7. 7
   Sonstigedried
8. 8
   Sonstigerecrystallized twice from ethanol

Vorschrift

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 (4) (0.8 g, 32 mmol) in a mixture of THF (35 mL) and triethylamine (3 mL). The reaction mixture was stirred in the boiling solvent 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 5 (0.18 g, 41%) 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, 2H), 6.95 (d, 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]+.

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