Synthesis of 9,9'-[1,2-ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6H-purin-6-one, an impurity of acyclovir.

Synthesis of 9,9'-[1,2-ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6H-purin-6-one, an impurity of acyclovir.

Molecules (Basel, Switzerland) (2012-07-27)

Rosa M Suárez, Maria Paz Matía, José Luis Novella, Andres Molina, Antonio Cosme, Juan José Vaquero, Julio Alvarez-Builla

PMID22832875

ABSTRACT

The synthesis of 9,9'-[1,2-ethanediylbis(oxymethylene)]bis-2-amino-1,9-dihydro-6H-purin-6-one, a minor impurity of acyclovir, is described. Starting with commercial N-(9-acetyl-6-oxo-1H-purin-2-yl)acetamide, the process uses an acid catalysed phase transfer catalysis (PTC) process to produce the selective alkylation at the 9 position of the guanine ring.

MATERIALS

Product Number

Brand

Product Description

268100

Sigma-Aldrich

Tetrabutylammonium phosphate monobasic solution, 1.0 M in H₂O

358665

Sigma-Aldrich

Tetrabutylammonium cyanide, 95%

86885

Sigma-Aldrich

Tetrabutylammonium perchlorate, ≥95.0% (T)

86880

Sigma-Aldrich

Tetrabutylammonium hydroxide solution, technical, ~40% in H₂O (~1.5 M)

86893

Supelco

Tetrabutylammonium perchlorate, for electrochemical analysis, ≥99.0%

86863

Sigma-Aldrich

Tetrabutylammonium hydroxide solution, 53.5-56.5% in H₂O

86854

Supelco

Tetrabutylammonium hydroxide solution, ~40% in water, suitable for ion chromatography

441244

Sigma-Aldrich

Paraformaldehyde, prilled, 95%

178780

Sigma-Aldrich

Tetrabutylammonium hydroxide solution, 40 wt. % in H₂O

155837

Sigma-Aldrich

Tetrabutylammonium hydrogensulfate, 97%

158127

Sigma-Aldrich

Paraformaldehyde, powder, 95%

230189

Sigma-Aldrich

Tetrabutylammonium hydroxide solution, 1.0 M in methanol

A3509

Sigma-Aldrich

2-Aminopurine, ≥99%

P6148

Sigma-Aldrich

Paraformaldehyde, reagent grade, crystalline

24-0630

Sigma-Aldrich

Paraformaldehyde, CP

79989

Sigma-Aldrich

Tetrabutylammonium cyanide, technical, ≥80%

86852

Supelco

Tetrabutylammonium chloride, suitable for ion pair chromatography, LiChropur^™, ≥99.0%

86853

Supelco

Tetrabutylammonium bisulfate, suitable for ion pair chromatography, LiChropur^™, ≥99.0%

86857

Supelco

Tetrabutylammonium bromide, suitable for ion pair chromatography, LiChropur^™, ≥99.0%

86833

Sigma-Aldrich

Tetrabutylammonium phosphate monobasic, puriss., 99% (T)

86870

Sigma-Aldrich

Tetrabutylammonium chloride, ≥97.0% (NT)

98479

Supelco

Tetrabutylammonium bisulfate solution, suitable for ion pair chromatography, LiChropur^™, concentrate, ampule

86890

Sigma-Aldrich

Tetrabutylammonium iodide, ≥99.0% (AT)

86903

Supelco

Tetrabutylammonium iodide, suitable for ion pair chromatography, LiChropur^™, ≥99.0%

72453

Sigma-Aldrich

Tetrabutylammonium bisulfate solution, ~55% in H₂O

359173

Sigma-Aldrich

Tetrabutylammonium nitrate, 97%

361399

Sigma-Aldrich

Tetrabutylammonium fluoride solution, 75 wt. % in H₂O

140775

Sigma-Aldrich

Tetrabutylammonium iodide, reagent grade, 98%

462144

Sigma-Aldrich

Tetrabutylammonium bromide solution, 50 wt. % in H₂O

193119

Sigma-Aldrich

Tetrabutylammonium bromide, ReagentPlus^®, ≥99.0%