2-Amino-6-chloro-4-pyrimidinol

Chemical Properties

White solid

Uses

2-Amino-6-chloro-4-pyrimidinol is used to prepare O- and N-phosphonomethoxyalkyl pyrimidines with antiviral activities. It is also used to synthesize (±)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine with antiherpetic activities.

Synthesis

General procedure for the synthesis of 2-amino-6-chloro-4-hydroxypyrimidines from 2-amino-4,6-dichloropyrimidines: to a suspension of 4,6-dichloropyrimidin-2-amine (21.2 g, 129.27 mmol) in 200 mL of aqueous 1N NaOH was added solid NaOH (4 g, 100.00 mmol) in batches. The reaction mixture was heated to reflux for 5 hours. After completion of the reaction, the mixture was cooled to room temperature in an ice water bath. The pH was slowly adjusted to 5-6 with aqueous CH3COOH. the reaction mixture was filtered and the precipitate collected. The solid product was washed with deionized water and subsequently dried in an oven under reduced pressure to give 17 g (86% yield) of 2-amino-6-chloro-4-hydroxypyrimidine as a white solid.

References

[1] Chemistry (Weinheim an der Bergstrasse, Germany), 2002, vol. 8, # 1, p. 293 - 301
[2] Organic Letters, 2009, vol. 11, # 1, p. 61 - 64
[3] Patent: WO2009/139834, 2009, A1. Location in patent: Page/Page column 93
[4] Journal of the Chemical Society, 1951, p. 3,6
[5] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 8, p. 1081 - 1083