Réaction #53377

Équation de réaction

ethyl acetate

Triethylamine

compound 14

3-(4-Hydroxyphenyl)propylamine hydrobromide

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

→

compound 15

Rendement 60.0%

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

Rendement 60.0%

Solvants

THF

MeOH

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture was stirred
2. 2
   Températureat reflux for 3 h
3. 3
   TempératureThe solution was then cooled to room temperature
4. 4
   Autrethe supernatant was isolated
5. 5
   AutreThe solvent was evaporated
6. 6
   Lavagethe 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
   AutreThe obtained solid was isolated by filtration
9. 9
   Autrethe precipitation of a yellow solid
10. 10
    Autrewhich was isolated by centrifugation
11. 11
    Lavagewashed with ethyl acetate
12. 12
    Autredried under vacuum

Mode opératoire

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]+.

Source