2,4-Dichloro-6-methyl-5-pyrimidinecarboxylic acid methyl ester
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2,4-Dichloro-6-methyl-5-pyrimidinecarboxylic acid methyl ester
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CAS No:
36745-93-4
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Formula:
C7H6Cl2N2O2
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Chemical Name:
2,4-Dichloro-6-methyl-5-pyrimidinecarboxylic acid methyl ester
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Synonyms:
(S)-methyl 2-(morpholin-3-yl)acetate HCL;methyl 2,4-dichloro-6-methylpyrimidine-5-carboxylatemethyl 2,4-dichloro-6-methylpyrimidine-5-carboxylate;2,4-Dichloro-6-methyl-5-pyrimidinecarboxylic acid methyl ester;Methyl 2,4-dichloro-6-methylpyrimidine-5-carboxylate;(3-BROMOPHENYL)(3-PYRIDINYL)METHANONE
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CAS No:
2,4-Dichloro-6-methyl-5-pyrimidinecarboxylic acid methyl ester Basic Attributes
221.04074
219.980637
DTXSID50727038
2933599090
2,4-Dichloro-6-methyl-5-pyrimidinecarboxylic acid methyl ester Use and Manufacturing
Preparation 1Methyl 2, 4-dichloro-6-methylpyrimidine-5-carboxylate To a suspension of methyl 6-methyl-2, 4-dioxo-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylate (1 g, 5.43 mmol) in POClSynthesis of compound 1.5. A solution of 1.4 (12.1 g, 0.06576 mol, 1.00 equiv) in phosphorusoxychloride (120ml) was heated at 110 °C for 2 hrs. After completion, reaction mixture was concentrated under reduced pressure and residue was quenched in ice. The crude product was extracted twice with ethyl acetate. The organic layers were dried over sodium sulfate and concentrated under reduced pressure to afford crude material which was purified by flash column chromatography This resulted in pure compound 1.5 (10.2g, 70.20percent>). MS (ES): m/z 222.8 [M+H]c) 4-Methyl-2, 6-dioxo-3H-pyrimidine-5-carboxylic acid methyl ester (0.64 g, 3.48 mmol) is dissolved in phosphoryl chloride (6.5 ml) and to it is added tributylamine (1.75 ml). The resulting mixture is heated at 95 °C for 3 h. Excess phosphoryl chloride is distilled of and ice-water is added to the reaction mixture and extracted with EtOAc (3 x 30 ml). The combined organic layers are washed with water (30 ml), brine (30ml), evaporated to dryness to get the crude product, which is purified by column chromatography (silica gel, 5percent /hexane) affording 2, 4-dichloro-6-methyl-pyrimidine-5-carboxylic acid methyl ester (0.45 g, 2.04 mmol, 59percent).
Computed Properties
Molecular Weight:221.04
XLogP3:2.4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:219.9806328
Monoisotopic Mass:219.9806328
Topological Polar Surface Area:52.1
Heavy Atom Count:13
Complexity:203
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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2,4-Dichloro-6-methyl-5-pyrimidinecarboxylic acid methyl ester
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