Synthesis of 1-Deazaguanine<sup>1</sup>

Gorton, Bert S.; Shive, William

doi:10.1021/ja01560a044

Cited by 17 publications

(15 citation statements)

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“…The removal of carbamates, by the use of different methods [12][13][14][15][16][17], has been described in the literature. The hydrolysis was first attempted in refluxing 40% aqueous potassium hydroxide, as indicated by Shevelev et al [5] for the corresponding methyl carbamate, and then 35% hydrochloric acid.…”

Section: Resultsmentioning

confidence: 99%

“…175-178 C [6]) 1 H NMR (DMSO-d 6 ) 9.81 (1H, s), 8.09 (1H, s), 7.73 (1H, s), 4.39 (2H, J = 7.2 Hz, q), 4.29 (2H, J = 6.8 Hz, q), 1.34 (3H, J = 6.8 Hz, t), 1.23 (3H, J = 6.8 Hz, t). 13 14.45. Satisfactory elemental analysis could not be obtained for this compound.…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR (DMSO-d 6 ) 9.85 (1H, s), 4.12 (2H, J = 6.8 Hz, q), 1.21 (3H, J = 7.2 Hz, t). 13 compound. However, the product of its deprotection in 60% H 2 SO 4 had the same spectral characteristics as described for 4-amino-3,5-dinitropyrazole, vide infra.…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR (DMSO-d 6 ) 8.56 (1H, s), 4.01 (2H, J = 7.0 Hz, q), 1.17 (3H, J = 7.0 Hz, t). 13 C NMR (DMSO-d 6 ) 162. 8, 154.5, 139.0, 122.8, 60.8, 14.9.…”

Section: Methodsmentioning

confidence: 99%

“…T m = 176 C (lit. [6] 175-178 C) 1 H NMR (DMSO-d 6 ) 7.14 (2H, s), 13 C NMR (DMSO-d 6 ) 131.75, 128. 4 4-Chloropyrazole (5).…”

Section: Methodsmentioning

confidence: 99%

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Four Syntheses of 4‐Amino‐3,5‐dinitropyrazole

Latypov

2014

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).In this paper, syntheses of 4-amino-3,5-dinitropyrazole from four different starting materials are described. The starting materials were 4-nitropyrazole, 4-nitro-3,5-dimethylpyrazole, 3,5-dinitropyrazole, and 4-chloropyrazole, respectively. They are compared in terms of yield, number of steps and suitability for scale-up into pilot scale production. The overall yield, calculated from commercially available starting materials, ranged from 21% in the case of synthesis via 3,5-dinitropyrazole up to 61% for the one starting from 4-chloropyrazole. With numerous factors taken into account, the latter was chosen for a pilot scale study and the product could be produced in batches of 200 g.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

“…1 H NMR (DMSO-d 6 ) 8.56 (1H, s), 4.01 (2H, J = 7.0 Hz, q), 1.17 (3H, J = 7.0 Hz, t). 13 C NMR (DMSO-d 6 ) 162. 8, 154.5, 139.0, 122.8, 60.8, 14.9.…”

Section: Methodsmentioning

confidence: 99%

“…T m = 176 C (lit. [6] 175-178 C) 1 H NMR (DMSO-d 6 ) 7.14 (2H, s), 13 C NMR (DMSO-d 6 ) 131.75, 128. 4 4-Chloropyrazole (5).…”

Section: Methodsmentioning

confidence: 99%

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Four Syntheses of 4‐Amino‐3,5‐dinitropyrazole

Latypov

2014

Journal of Heterocyclic Chem

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Reaktionen mit Chelidonsäure III. Über Umsetzungen von Pyranyliden‐carbonsäurederivaten mit Diaminen. 10. Mitt. über Untersuchungen an γ‐Pyronen

Eiden¹,

Pusztai²

1966

Archiv der Pharmazie

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Reuktionen mit Chdidonsiiure ZZZ 139 289. Bd. rees/zS p e k t r e n zu Tab. 2 1.6 ml VIII in Aceton (0,00408 mg/ml) wurden mit 1 Tr. 0,5 n methanol. KOH versetat.Schichtdicke 0,4 cm.2.100 mg VIII in 20 ml Athmol warm geliist, mit 2 Tr. Piperidin versetat. Schichtdicke 0,2 om.3.100 mg VLII und 100 mg XI1 in 20 ml Athanol warm gelast, mit 2 Tr. Piperidin ver-&at. Schichtdicke 0,2 cm. Es tritt schnell Trtibung, Verfiirbung und Kristalliaation ein.4.100 mg XIV in 10 ml Athano1 warm gelht, mit 3 Tr. Piperidin versetzt. Schichtdicke 0,2 om. 5.5 ml XIII in Aceton (0,01032 mg/ml) d e n rnit 1 Tr. n methanol. NaOCH, versetat. Schichtdicke 0,4 cm.6.100 mg ViFf und 0,l ml XV in 10 ml Athanol warm gelht, mit 10 Tr. Piperidin veraetzt. Scbhtdicke 0,2 om. 7. 5 ml XVIII in Aceton (0,01825 mg/ml) wurden mit 1 !Cr. n methanol. NaOCH, veraetzt. Schichtdicke 0,2 cm. 8.100 mg VIII und 100 mg XVI in 10 ml Athano] warm gelast, mit 5 Tr. Piperidin versetat. Schichtdicke 0,2 cm. 9.5 ml XIX in Aceton (0,01791 mg/ml) wurden mit 1 Tr. n methanol. NaOCH, vemtzt. Schichtdicke 0,2 cm.

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