Reaktion #53377

Reaktionsgleichung

ethyl acetate

Triethylamine

compound 14

3-(4-Hydroxyphenyl)propylamine hydrobromide

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

→

compound 15

Ausbeute 60.0%

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

Ausbeute 60.0%

Lösungsmittel

THF

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred
2. 2
   Temperaturat reflux for 3 h
3. 3
   TemperaturThe solution was then cooled to room temperature
4. 4
   Sonstigethe supernatant was isolated
5. 5
   SonstigeThe solvent was evaporated
6. 6
   Waschenthe residual oil was washed with ether (2×50 mL), ethyl acetate (50 mL)
7. 7
   workup.ADDITIONtreated with 20 ml of 10% HCl
8. 8
   SonstigeThe obtained solid was isolated by filtration
9. 9
   Sonstigethe precipitation of a yellow solid
10. 10
    Sonstigewhich was isolated by centrifugation
11. 11
    Waschenwashed with ethyl acetate
12. 12
    Sonstigedried under vacuum

Vorschrift

Triethylamine (8 mL) was added to suspension of compound 14 (0.470 g, 2 mmol) in THF (40 mL) and the mixture was stirred at room temperature for 15 min. After this time 1-(3,5-diamino-6-chloropyrazinoyl-2-methyl-pseudothiourea hydroiodide (0.15 g, 0.4 mmol) was added and the mixture was stirred at reflux for 3 h. The solution was then cooled to room temperature and the supernatant was isolated. The solvent was evaporated and the residual oil was washed with ether (2×50 mL), ethyl acetate (50 mL) and treated with 20 ml of 10% HCl. The obtained solid was isolated by filtration and dissolved in MeOH (approx. 50 mL). Addition of ethyl acetate (20 mL) to the solution caused the precipitation of a yellow solid, which was isolated by centrifugation, washed with ethyl acetate and dried under vacuum to give compound 15 (48 mg, 31%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ1.80 (br s, 2H), 2.58 (m, 2H), 3.95 (br s, 4H), 6.70 (d, 2H), 7.03 (d, 2H), 7.48 (br. s, 2H), 8.80 (br s, 1H), 8.93 (br s, 1H), 9.32 (br s, 2H), 10.52 (s, 1H). APCI MS m/z=364 [C15H18ClN7O2+H]+.

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