| Identification | More | [Name]
2-Amino-6-chloro-4-pyrimidinol | [CAS]
1194-21-4 | [Synonyms]
2-AMINO-4-CHLORO-6-HYDROXYPYRIMIDINE
2-AMINO-4-CHLORO-6-PYRIMIDINOL
2-AMINO-4-HYDROXY-6-CHLOROPYRIMIDINE
2-AMINO-6-CHLORO-4-HYDROXYPYRIMIDINE
AKOS 92811
TIMTEC-BB SBB004114
2-amino-6-chloro-4(1h)-pyrimidinon
2-amino-6-chloro-4-pyrimidino
2-amino-6-chloro-4-pyrimidinol
2-amino-6-chloropyrimidin-4-ol hydrate
4(1H)-Pyrimidinone, 2-amino-6-chloro-(9CI)
4-Pyrimidinol, 2-amino-6-chloro.
2-AMINO-6-CHLORO-4-PYRIMIDINOL HYDRATE PURUM 98%
2-AMINO-6-CHLORO-4-PYRIMIDINOL MONOHYDRATE 95%
2-Amino-6-chloro-4(1H)-pyrimidinone
2-Amino-6-chloro-4(3H)-pyrimidinone
6-Chloroisocytosine | [EINECS(EC#)]
214-785-4 | [Molecular Formula]
C4H4ClN3O | [MDL Number]
MFCD00006093 | [Molecular Weight]
145.55 | [MOL File]
1194-21-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
252 °C (dec.)(lit.) | [Boiling point ]
259.1±50.0 °C(Predicted) | [density ]
1.7910 (rough estimate) | [refractive index ]
1.4510 (estimate) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
DMSO (Sparingly) | [form ]
Solid | [pka]
7.49±0.50(Predicted) | [color ]
Pale Yellow | [Detection Methods]
HPLC | [Stability:]
Hygroscopic | [InChI]
InChI=1S/C4H4ClN3O/c5-2-1-3(9)8-4(6)7-2/h1H,(H3,6,7,8,9) | [InChIKey]
VBWACOJLJYUFKJ-UHFFFAOYSA-N | [SMILES]
C1(N)NC(Cl)=CC(=O)N=1 | [CAS DataBase Reference]
1194-21-4(CAS DataBase Reference) | [Storage Precautions]
Store under nitrogen |
| Hazard Information | Back Directory | [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 |
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