ChemicalBook CAS DataBase List 6-Amino-9H-purine-9-propanoic acid

6-Amino-9H-purine-9-propanoic acid synthesis

6synthesis methods

Product Name:6-Amino-9H-purine-9-propanoic acid
CAS Number:4244-47-7
Molecular formula:C8H9N5O2
Molecular Weight:207.19

3-(9-Adeninyl)propionoic Acid Ethyl Ester

7083-40-1
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4244-47-7
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Yield:4244-47-7 95%

Reaction Conditions:

with hydrogenchloride in water; pH=3; for 3 h;Reflux;

Steps:

3-(6-Aminopurine-9-yl)-propionic acid, (AA)

3-(6-Aminopurine-9-yl)-propionic acid, (AA). A mixture of compound 1(a) (5 g, 21.3 mmol) and 200 ml aqueous 3 M HCl solution was refluxed for 3 h, then cooled to room temperature. The mixture's pH was adjusted to 3.0 by careful addition of solid NaOH. The precipitate was collected by buchner filtration, recrystallized from hot water, washed with cold water and dried under reduced pressure. Compound AA was obtained as a white solid (4.19 g, 95%), m.p. 272-274 °C. 1H NMR (300 MHZ, D₂O): 2.79-2.81 (t, 2H), 4.44-4.49 (t, 2H), 8.16 (s, 1H), 8.27 (s, 1H). 13C NMR (75 MHZ, D₂O): 43.88 (CH₂), 57.05 (CH₂), 145.90, 153.7, 157.6 (Ar-C, Ar-CH), 174.32 (C). FT-IR (KBr, cm-1): 1698 (ν_C=O), 3219 (ν_{O-H stretch}), 1408 (ν_{O-H bend}), 1224 (ν_C-O), 1611, 3318 (ν_N-H), 1509 (ν_C=N).