| Identification | More | [Name]
2-Chloro-4-methylpyrimidine | [CAS]
13036-57-2 | [Synonyms]
2-CHLORO-4-METHYLPYRIMIDINE
Pyrimidine, 2-chloro-4-methyl-(6CI,7CI,8CI,9CI)
2-CHLORO-4-METHYLPYRIMIDINE 98%
2-Chloro-6-methylpyrimidine | [Molecular Formula]
C5H5ClN2 | [MDL Number]
MFCD00054434 | [Molecular Weight]
128.56 | [MOL File]
13036-57-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Pale Yellow Solid | [Melting point ]
35-36°C | [Boiling point ]
94°C/17mmHg(lit.) | [density ]
1.234±0.06 g/cm3(Predicted) | [Fp ]
98℃ | [storage temp. ]
Keep Cold/Store under Nitrogen | [solubility ]
Chloroform | [form ]
Solid | [pka]
-0.93±0.20(Predicted) | [color ]
Pale Yellow to Beige | [Sensitive ]
Moisture Sensitive | [Stability:]
Toxic | [InChI]
InChI=1S/C5H5ClN2/c1-4-2-3-7-5(6)8-4/h2-3H,1H3 | [InChIKey]
BHAKRVSCGILCEW-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NC=CC(C)=N1 | [CAS DataBase Reference]
13036-57-2(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Pale Yellow Solid | [Uses]
2-Chloro-4-methylpyrimidine (cas# 13036-57-2) is a compound useful in organic synthesis. | [Application]
2-chloro-4-methylpyrimidine could be used to synthesis 4-Methyl-2-vinylpyrimidine which is a intermediate of pyrimidinyl trans-cyclopropane carboxylic acid (rac-1)[1].
| [Synthesis]
Step A: Synthesis of 2-chloro-4-methylpyrimidine
To a vigorously stirred slurry containing 50.0 g (0.31 mol) of 2,6-dichloro-4-methylpyrimidine, 250 mL of ethanol (EtOH), and 250 mL of water, 41 g (0.63 mol) of zinc powder and 0.78 g (3.08 mmol) of iodine were sequentially added. The reaction mixture was heated to reflux at 70°C for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure to remove ethanol and subsequently extracted with dichloromethane (DCM). The organic layers were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to remove solvent. The residue was purified by silica gel column chromatography using a hexane/DCM solvent mixture as eluent, resulting in 20.6 g (53% yield) of 2-chloro-4-methylpyrimidine as a white solid. The structure of the product was confirmed by 1H-NMR (d6-DMSO, 400 MHz) δ 8.59 (d, 1H, J=4.9 Hz), 7.44 (d, 1H, J=4.9 Hz), and 3.29 (s, 3H), and ESIMS: 129.11 (M+H+). | [References]
[1] M. Fray. “N-Ylide Mediated Synthesis and Resolution of a Chiral Pyrimidinyl Cyclopropane Carboxylic Acid.” Organic Process Research &Development 19 1 (2023). |
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