ChemicalBook CAS DataBase List N-Benzoylaminopurine

N-Benzoylaminopurine synthesis

3synthesis methods

Product Name:N-Benzoylaminopurine
CAS Number:4005-49-6
Molecular formula:C12H9N5O
Molecular Weight:239.23

Benzoyl chloride (1.3 mL, 11 mmol) was added dropwise over 30 min to a stirred suspension of adenine (1.35 g, 10 mmol) in dry pyridine, and stirring was continued at 100 °C for a further 3 h, and the reaction mixture was allowed to stand overnight at room temperature. The reaction was quenched with methanol and the solvents were removed under reduced pressure. The residue was triturated in hot isopropanol and dried in vacuo to give 8 as a white solid: yield 2.15 g (90%). MS (+ESI): m/z 240 [M+H]+; 1H NMR (400 MHz, d-DMSO): δ11.50 (s, 1H), 8.74 (s, 1H), 8.52 (s, 1H), 8.11 (d, 2H, J = 7.2 Hz), 7.66 (t, 1H, J = 7.2 Hz), 7.58 (t, 2H, J = 7.2 Hz).
N-Benzoylaminopurine synthesis.jpg

Benzamide, N-[9-[3-C-ethenyl-3,5-O-(1-methylethylidene)-β-D-xylofuranosyl]-9H-purin-6-yl]-

188486-36-4
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4005-49-6
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$11.00/5g

Yield:-

Steps:

Multi-step reaction with 6 steps
1.1: 97 percent / pyridine / 0 - 20 °C
2.1: ozone / CH₂Cl₂ / 1 h / -78 °C
2.2: 69 percent / Me₂S / CH₂Cl₂ / 1 h / -78 - 20 °C
3.1: 91 percent / KMnO₄; phosphate buffer / 2-methyl-propan-2-ol; H₂O / 0.5 h / 20 °C / pH 7
4.1: NEt₃; phenyl dichlorophosphate / tetrahydrofuran / 1 h / 0 °C
4.2: 72 percent / NEt₃ / tetrahydrofuran / 0.5 h / 0 °C
5.1: 86 percent / trifluoroacetic acid; water / 0.5 h / 20 °C
6.1: 84 percent Spectr_. / Bu₃SnH / methanol / 3 h / 20 °C / Photolysis

References:

Lenz, Roman;Giese, Bernd [Journal of the American Chemical Society,1997,vol. 119,# 12,p. 2784 - 2794]

Adenosine, 2',5'-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-

65109-11-7
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4005-49-6
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Benzamide, N-[9-(3-C-ethenyl-β-D-xylofuranosyl)-9H-purin-6-yl]-

188486-35-3
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4005-49-6
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$11.00/5g

References

N-Benzoylaminopurine Related Search:

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