Reaction #53384

Reaction equation

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

27

4-(3,4-Dihydroxyphenyl)butyl amine hydrobromide

→

compound 28

Yield 51.0%

4-(3,4-Dihydroxyphenyl)butylamidino-3,5-diamino-6-chloropyrazinecarboxamide hydrochloride

Yield 51.0%

Solvents

THF

triethylamine

Conditions

Workup

1. 1
   Temperatureat reflux for 3 h
2. 2
   Otherthe supernatant was separated
3. 3
   Otherthe solvent was removed under reduced pressure
4. 4
   WashThe brown residue was washed with ether (2×30 mL)
5. 5
   workup.ADDITIONfollowed by addition of 10% HCl (5 mL)
6. 6
   OtherThe solid material was collected
7. 7
   workup.DISSOLUTIONdissolved in methanol
8. 8
   Otherprecipitated by addition of ethyl acetate
9. 9
   WashThe precipitate was washed with 10% HCl
10. 10
    Otherdried

Procedure

1-(3,5-Diamino-6-chloropyrazinoyl-2-methyl-pseudothiourea hydroiodide (0.2 g, 0.51 mmol) was added to a suspension of 27 in a mixture of THF (35 mL) and triethylamine (3 mL). The reaction mixture was stirred at reflux for 3 h, then the supernatant was separated and the solvent was removed under reduced pressure. The brown residue was washed with ether (2×30 mL) followed by addition of 10% HCl (5 mL). The solid material was collected, dissolved in methanol and precipitated by addition of ethyl acetate. The precipitate was washed with 10% HCl and dried to give compound 28 (131 mg, 51%) as a beige solid. 1H NMR (300 MHz, DMSO-d6) δ1.52 (br s, 4H), 2.42 (m, 2H), 3.31 (m, 2H), 6.43 (m, 1H), 6.61 (m, 2H), 7.42 (br s, 2H), 7.90 (br s, 1H), 8.82 (br s, 1H), 8.98 (br s, 1H), 9.25 (s, 1H) 10.52 (s, 1H), APCI MS m/z=394 [C16H20ClN7O3+H]+.

Source