| Identification | Back Directory | [Name]
6-(PYRIDIN-3-YL)PYRIMIDIN-4-AMINE | [CAS]
1192814-34-8 | [Synonyms]
6-(PYRIDIN-3-YL)PYRIMIDIN-4-AMINE 4-Pyrimidinamine, 6-(3-pyridinyl)- | [Molecular Formula]
C9H8N4 | [MDL Number]
MFCD21234637 | [MOL File]
1192814-34-8.mol | [Molecular Weight]
172.19 |
| Chemical Properties | Back Directory | [Boiling point ]
422.3±35.0 °C(Predicted) | [density ]
1.259±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C(protect from light) | [pka]
3.75±0.10(Predicted) |
| Hazard Information | Back Directory | [Uses]
6-(Pyridin-3-yl)pyrimidin-4-amine is used as a reactant in the preparation of quinuclidine compounds as α7 nicotinic acetylcholine receptor ligands for treating central nervous system disorders. | [Synthesis]
Step A: Synthesis of 6-(pyridin-3-yl)pyrimidin-4-amine
6-Chloropyrimidin-4-amine (0.324 g, 2.5 mmol), pyridine-3-boronic acid (0.384 g, 3.13 mmol), sodium carbonate (0.795 g, 7.50 mmol), and bis(triphenylphosphine)palladium(II) chloride (0.035 g, 0.050 mmol) were suspended in a mixture of DME/EtOH/water (v/v ratio not specified) solvent. The reaction mixture was heated at 125 °C for 20 min in a microwave synthesizer and subsequently concentrated. The crude product was purified by silica gel column chromatography with an elution gradient of 10-60% ethyl acetate in hexane solution, followed by 5-25% 9:1 methanol:ammonium hydroxide-ethyl acetate mixed solvent. The final product was 6-(pyridin-3-yl)pyrimidin-4-amine (0.17 g, 0.987 mmol) in 40% yield as an off-white solid.LCMS analysis showed a retention time (R.T.) of 0.31 min and a molecular ion peak [M+H]+ of 173.11. The final product was purified using an elution gradient of 10-60% ethyl acetate in hexane. | [References]
[1] Patent: WO2011/53292, 2011, A1. Location in patent: Page/Page column 249 [2] Patent: JP5714745, 2015, B2. Location in patent: Paragraph 0445; 0446 [3] Patent: WO2011/56503, 2011, A1. Location in patent: Page/Page column 49 |
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Energy Chemical
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Synthonix Inc
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A.J Chemicals
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