Reaktion #53420

Reaktionsgleichung

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

amine

4-[4-(2-Hydroxyethyloxy)phenyl]butylamine

methanol

diisopropylethylamine

→

compound 116

Ausbeute 194.0%

butylamidino-3,5-diamino-6-chloropyrazinecarboxamide Hydrochloride

Ausbeute 194.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 3.5 h
2. 2
   SonstigeThe formed precipitate was isolated
3. 3
   Waschenwashed with ethyl acetate (2×5 mL)
4. 4
   workup.ADDITIONtreated with 5% HCl (10 mL)
5. 5
   SonstigeThe resulting solid was isolated by filtration
6. 6
   Waschenwashed with water
7. 7
   Sonstigedried under vacuum

Vorschrift

1-(3,5-Diamino-6-chloropyrazinoyl-2-methyl-pseudothiourea hydroiodide (0.32 g, 0.8 mmol) was added to a solution of amine 115 (0.25 g, 1.2 mmol) in a mixture of THF (15 mL), methanol (5 mL) and diisopropylethylamine (1 mL). The reaction mixture was stirred at reflux for 3.5 h and then cooled to room temperature. The formed precipitate was isolated, washed with ethyl acetate (2×5 mL) and treated with 5% HCl (10 mL). The resulting solid was isolated by filtration, washed with water and dried under vacuum to give compound 116 (0.25 g, 73%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 1.56 (m, 4H), 2.57 (m, 2H), 3.32 (m, 2H), 3.70 (m, 2H), 3.93 (m, 2H), 4.90 (t, 1H), 6.84 (d, 2H), 7.12 (d, 2H), 7.45 (s, 2H), 8.70 (br s, 1H), 8.88 (br s, 1H), 9.12 (br s, 1H) 10.45 (s, 1H). APCI MS m/z=422 [C18H24ClN7O3+H]+.

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