Methyl 6-HydroxypyriMidine-4-carboxylate synthesis
- Product Name:Methyl 6-HydroxypyriMidine-4-carboxylate
- CAS Number:7399-93-1
- Molecular formula:C6H6N2O3
- Molecular Weight:154.12
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7399-93-1
Step 9A: Synthesis of methyl 6-oxo-1,6-dihydropyrimidine-4-carboxylate. 6-Hydroxy-4-pyrimidinecarboxylic acid (36.0 g, 257 mmol) was dissolved in methanol (360 mL), and chlorotrimethylsilane (56 g, 554 mmol) was slowly added dropwise. The reaction mixture was stirred at room temperature for 8 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residual solid was mixed with 200 mL of methanol and refluxed for 30 minutes. After cooling to room temperature, the precipitated solid was collected by filtration and washed with a small amount of methanol. The product was dried under vacuum at 35 °C to give 27.9 g (70% yield) of methyl 6-oxo-3,6-dihydropyrimidine-4-carboxylate.1H NMR (300 MHz, DMSO-d6) data were as follows: δ (ppm) 12.50 (broad single peak, 1H), 8.23 (single peak, 1H), 6.83 (single peak, 1H), 3.80 (single peak, 3H).
67-56-1
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7399-93-1
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Yield:7399-93-1 70%
Reaction Conditions:
with chloro-trimethyl-silane at 20; for 8 h;
Steps:
33.2
Example 33.2Pyridazine-4-carboxylic acid ethyl ester To 6-pyrimidine-4-carboxylic acid (36.0 g, 257 mmol) in methanol (360 mL) was dropwise added chlorotrimethylsilane (56 g, 554 mmol) and then stirred for 8 hours at room temperature. The solvent was evaporated off and the solid was refluxed with 200 mL methanol for 30 minutes. The reaction mixture was cooled, the precipitated solid was filtered off and washed with a small amount of methanol and dried under vacuum at 35° C. to afford 27.9 g (70%) of the title compound.1H NMR (300 MHz, (CD3)2SO): δ (ppm) 12.50 (broad s, 1H), 8.23 (s, 1H), 6.83 (s, 1H), 3.80 (s, 3H).
References:
AstraZeneca AB;NPS PHARMACEUTICALS, INC. US2007/259862, 2007, A1 Location in patent:Page/Page column 40
67-56-1
782 suppliers
$7.29/5ml-f
6299-87-2
199 suppliers
$6.00/100mg
7399-93-1
88 suppliers
$31.00/250mg