1683-85-8 | 2-Pyrimidinamine, 5-fluoro- (9CI)

CAS:1683-85-8 | 2-Pyrimidinamine, 5-fluoro- (9CI),Description

5-Fluoropyrimidin-2-amine is a chemical compound with the molecular formula C4H4FN3. It has a molecular weight of 113.09. It is used in the synthesis of various pharmaceutical compounds.

Synthesis Analysis

The synthesis of 5-Fluoropyrimidin-2-amine involves the selective fluorination of 4-substituted 2-aminopyrimidine derivatives with Selectfluor in the presence of Ag2CO3. The substrates are 4-aryl- or vinyl- or amine-substituted 2-aminopyrimidines. This method gives 4-substituted 5-fluoro-2-aminopyrimidines in fair to high yields with excellent regioselectivities.

Molecular Structure Analysis

The InChI code for 5-Fluoropyrimidin-2-amine is 1S/C4H4FN3/c5-3-1-7-4(6)8-2-3/h1-2H, (H2,6,7,8) and the InChI key is FUNBZJKZJGKXQB-UHFFFAOYSA-N.

Physical And Chemical Properties Analysis

5-Fluoropyrimidin-2-amine is a solid at room temperature. Unfortunately, specific data on its boiling point, melting point, and density were not available.

Scientific Research Applications

Synthesis and Kinase Inhibition

5-Fluoropyrimidin-2-amine derivatives show promise as potential kinase inhibitors, which are crucial in cancer therapy. The facile and regioselective synthesis of novel 2,4-disubstituted-5-fluoropyrimidines has been achieved, highlighting their role in anticancer agents similar to 5-fluorouracil (5-FU) (Wada et al., 2012).

Biocatalysis in Drug Synthesis

The immobilized amine transaminase from Vibrio fluvialis has been used for the synthesis of (S)‐1‐(5‐fluoropyrimidin‐2‐yl)‐ethanamine, a key intermediate in JAK2 kinase inhibitor AZD1480. This method demonstrates a greener approach to synthesizing this compound, offering an alternative to traditional chemical synthesis (Semproli et al., 2020).

Deoxycytidine Kinase Inhibitors

5-Fluoropyrimidin-2-amine is a key intermediate in the preparation of potent deoxycytidine kinase (dCK) inhibitors. A practical synthesis route for this compound has been developed, showcasing its significance in creating new classes of dCK inhibitors, which are essential in cancer treatment (Zhang et al., 2009).

Safety And Hazards

5-Fluoropyrimidin-2-amine is classified as harmful if swallowed, causes serious eye irritation, and may cause respiratory irritation. Precautionary measures include avoiding breathing dust/fume/gas/mist/vapors/spray, wearing protective gloves/protective clothing/eye protection/face protection, and if in eyes, rinsing cautiously with water for several minutes.

Future Directions

5-Fluoropyrimidin-2-amine has been used in the synthesis of a key intermediate of the JAK2 kinase inhibitor AZD1480. This suggests potential applications in the development of new pharmaceuticals, particularly in the field of oncology.

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