反応 #53377

反応方程式

ethyl acetate

Triethylamine

compound 14

3-(4-Hydroxyphenyl)propylamine hydrobromide

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

→

compound 15

収率 60.0%

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

収率 60.0%

溶媒

THF

MeOH

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred
2. 2
   温度at reflux for 3 h
3. 3
   温度The solution was then cooled to room temperature
4. 4
   その他the supernatant was isolated
5. 5
   その他The solvent was evaporated
6. 6
   洗浄the 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
   その他The obtained solid was isolated by filtration
9. 9
   その他the precipitation of a yellow solid
10. 10
    その他which was isolated by centrifugation
11. 11
    洗浄washed with ethyl acetate
12. 12
    その他dried under vacuum

実験手順

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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