Реакция #53377

Уравнение реакции

ethyl acetate

Triethylamine

compound 14

3-(4-Hydroxyphenyl)propylamine hydrobromide

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

→

compound 15

Выход 60.0%

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

Выход 60.0%

Растворители

THF

MeOH

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe mixture was stirred
2. 2
   Температураat reflux for 3 h
3. 3
   ТемператураThe solution was then cooled to room temperature
4. 4
   Другоеthe supernatant was isolated
5. 5
   ДругоеThe solvent was evaporated
6. 6
   Промывкаthe 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
   ДругоеThe obtained solid was isolated by filtration
9. 9
   Другоеthe precipitation of a yellow solid
10. 10
    Другоеwhich was isolated by centrifugation
11. 11
    Промывкаwashed with ethyl acetate
12. 12
    Другоеdried under vacuum

Методика

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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