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Chemical Structure| 157981-55-0 Chemical Structure| 157981-55-0

Structure of 157981-55-0

Chemical Structure| 157981-55-0

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Product Details of [ 157981-55-0 ]

CAS No. :157981-55-0
Formula : C8H10N2O3
M.W : 182.18
SMILES Code : O=C(C1=C(C)N=CNC1=O)OCC

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Application In Synthesis of [ 157981-55-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 157981-55-0 ]

[ 157981-55-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 6313-33-3 ]
  • [ 3044-06-2 ]
  • [ 157981-55-0 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In ethanol; water; at 20℃; for 48h; Reference Example 196 Ethyl 4-hydroxy-6-methylpyrimidine-5-carboxylate A mixture of diethyl malonate (4.8 mL), triethyl orthoacetate (17 mL), acetic anhydride (0.11 mL) and zinc chloride (1.2 g) was stirred at 140C. To the mixture was added acetic anhydride (0.11 mL) each after 30, 90 and 120 minutes, and then stirred at the same temperature overnight. The reaction mixture was cooled to room temperature, and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 4/1 - 7/3) to give <strong>[3044-06-2]diethyl 2-(1-ethoxyethylidene)malonate</strong> (5.02 g). To a solution of <strong>[3044-06-2]diethyl 2-(1-ethoxyethylidene)malonate</strong> (4.13 g) in ethanol (15 mL) were added formamidine hydrochloride (1.73 g) and a solution of potassium hydroxide (2.21 g) in water (7.5 mL), and the mixture was stirred at room temperature for 2 days. The reaction mixture was neutralized by adding acetic acid. To the mixture was added ethyl acetate (30 mL), and the mixture was stirred at room temperature for 30 minutes. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate - ethyl acetate/methanol = 9/1) to give the title compound (1.5 g).
  • 2
  • [ 157981-55-0 ]
  • [ 157981-60-7 ]
  • 3
  • [ 3473-63-0 ]
  • [ 3044-06-2 ]
  • [ 157981-55-0 ]
  • 4
  • [ 157981-55-0 ]
  • [ 157981-60-7 ]
YieldReaction ConditionsOperation in experiment
53.78% With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 25℃; for 0.5h; DMF (3.0 mL, 27.5 mmol) was dissolved in dichloromethane (250 mL).Oxalyl chloride (8.1 mL, 82.5 mmol) was slowly added dropwise under ice bath.The reaction was heated to 25 C and stirred for 30 min to give the compound 4-hydroxy-6-methylpyrimidine-5-formate B.Add the ester (10.0 g, 55 mmol), stir the reaction at 25 C for 12.0 h, add water (50 mL),The organic layer was separated, and the organic layer was washed once with saturated brine (30 mL).The organic phase was dried over anhydrous sodium sulfate (20 g) and concentrated.The concentrate was subjected to column chromatography (eluent: CH 2 Cl 2 / MeOH (v/v) = 45 / 1) to afford 5.9 g of pale yellow oil. Yield: 53.78%.
 

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