ChemicalBook--->CAS DataBase List--->1192814-34-8

1192814-34-8

1192814-34-8 Structure

1192814-34-8 Structure
IdentificationBack 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 PropertiesBack 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)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302
[Precautionary statements ]

P280-P305+P351+P338
Hazard InformationBack 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]

4-Amino-6-chloropyrimidine

5305-59-9

3-Pyridylboronic acid

1692-25-7

6-(PYRIDIN-3-YL)PYRIMIDIN-4-AMINE

1192814-34-8

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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