Reaction #53380

Reaction equation

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

21

5-(4-Hydroxyphenyl)pentyl amine

→

22

Yield 131.5%

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

Yield 131.5%

Solvents

methanol

THF

Conditions

Workup

1. 1
   Temperatureat reflux for 2 h
2. 2
   Otherthe solvent was removed under reduced pressure
3. 3
   Washthe resulting oil was washed with ether (2×50 mL)
4. 4
   workup.ADDITIONtreated with ethyl acetate until a yellow powder
5. 5
   Otherwas formed
6. 6
   Otherthe volume was slowly reduced until precipitation
7. 7
   Otherthe precipitate was collected by centrifugation
8. 8
   workup.ADDITIONDiluted HCl (20 mL of a 10% solution) was added
9. 9
   workup.STIRRINGthe mixture was vigorously stirred for 20 min
10. 10
    Filtrationthe precipitate was filtered off
11. 11
    Washwashed with cold water
12. 12
    Otherdried

Procedure

1-(3,5-Diamino-6-chloropyrazinoyl-2-methyl-pseudothiourea hydroiodide (0.25 g, 0.65 mmol) was added to a solution of 21 (0.6 g, 3.4 mmol) in THF (50 mL). The reaction mixture was stirred at reflux for 2 h, then the solvent was removed under reduced pressure and the resulting oil was washed with ether (2×50 mL) and treated with ethyl acetate until a yellow powder was formed. The yellow solid was dissolved in methanol (70 mL) and the volume was slowly reduced until precipitation began (approximately 25 mL). The solution was cooled to 0° C. and the precipitate was collected by centrifugation. Diluted HCl (20 mL of a 10% solution) was added and the mixture was vigorously stirred for 20 min, then the precipitate was filtered off, washed with cold water, and dried to give 22 (183 mg, 39%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ1.32 (br s, 2H), 1.55 (m, 4H), 2.45 (m, 2H), 3.29 (m, 2H), 6.68 (d, 2H), 6.97 (d, 2H), 7.46 (s, 1H), 8.00 (br s, 1H), 8.83 (br s, 1H), 8.97 (br s, 1H), 9.46 (d, 2H), 10.55 (s, 1H). APCI MS m/z=392[C17H22ClN7O2+H]+.

Source