Reaction #53411

Reaction equation

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

67

4-(4-Hydroxymethylphenyl)butylamine

→

68

Yield 194.0%

4-(4-Hydroxymethylphenyl)butylamidino-3,5-diamino-6-chloropyrazinecarboxamide Hydrochloride

Yield 194.0%

Solvents

THF

Conditions

Workup

1. 1
   Temperatureat reflux for 3 h
2. 2
   Otherthe solvent was evaporated
3. 3
   WashThe residue was washed with ethyl acetate (3×15 mL)
4. 4
   Otherdried
5. 5
   workup.ADDITIONtreated with 3% HCl (15 mL)
6. 6
   OtherThe yellow solid that formed
7. 7
   Filtrationwas filtered
8. 8
   Washwashed with water (2×10 mL)
9. 9
   Otherdried

Procedure

1-(3,5-Diamino-6-chloropyrazinoyl-2-methyl-pseudothiourea hydroiodide (0.2 g, 0.52 mmol) was added to an anhydrous THF suspension (20 mL) of 67 (0.37 g, 2.06 mmol). The reaction mixture was stirred at reflux for 3 h then the solvent was evaporated. The residue was washed with ethyl acetate (3×15 mL), dried and treated with 3% HCl (15 mL). The yellow solid that formed was filtered, washed with water (2×10 mL) and dried to provide 68 (216 mg, 98%). 1H NMR (300 MHz, DMSO-d6) δ 1.57 (br s, 4H), 2.62 (m, 2H), 3.35 (m, 2H), 3.73 (br s, 4H), 4.45 (s, 2H), 7.12 (d, 2H), 7.24 (d, 2H), 8.85 (br s, 1H), 9.98 (br s, 1H), 9.32 (br s, 1H), 10.55 (s, 1H). APCI MS m/z 392 [C17H22ClN7O3+H]+.

Source