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Chemical Structure| 21038-67-5

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Product Details of [ 21038-67-5 ]

CAS No. :21038-67-5
Formula : C7H5N3O2
M.W : 163.13
SMILES Code : C1=CN=CC2=C1C(=O)NC(=O)N2
MDL No. :MFCD07438024
InChI Key :MNNWQAIAFUMNOS-UHFFFAOYSA-N
Pubchem ID :278397

Safety of [ 21038-67-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of [ 21038-67-5 ]

* 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 [ 21038-67-5 ]

[ 21038-67-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 21038-67-5 ]
  • [ 908240-50-6 ]
YieldReaction ConditionsOperation in experiment
82% With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In toluene; at 25℃; for 18h; To a mixture of pyrido[3,4-d]pyrimidine-2,4(1 H,3H)-dione (2b, 20.00 g, 122.60 mmol) and POCI3 (328.03 g, 2.14 mol) in toluene (200 mL) was added DIEA (31 .69 g, 245.20 mmol) dropwise and this reaction mixture stirred at 25°C overnight (18hr) to give suspension. The solvent and POCI3 was removed under vacuum, diluted with DCM (50 mL), neutralized with DIEA to pH=7 at -20°C and concentrated again, the residue was purified by column (20-50percent EA/PE) to give the product (2c, 20.00g, 99.99 mmol, 82percent yield) as a yellow solid. 1 H NMR (400 MHz, CHLOROFORM-d) delta 9.52 (s, 1 H), 8.92 (d, J=5.6 Hz, 1 H), 8.04 (d, J=5.6 Hz, 1 H). LCMS (m/z [M+H]+): 200.0.
41% With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In toluene;Reflux; To a mixture of pyrido[3,4-d]pyridine-2,4(1H,3H)-dione (2.0 g, 12.3 mmol) in toluene (50 mL) was added DIEA (3.15 g, 25 mmol) and POC13 (9.5 g, 61.4 mmol). The reaction mixture was refluxed overnight. The solution was concentrated in vacuo and the residue was taken in ethyl acetate, washed with aq. NaHCO3 and brine. The organics were dried and concentrated. The residue was purified by silica gel chromatography (25percent EA:PE)to give 1.0 g (41percent) of the title compound. ?H NMR (400 MHz, DMSO-d6): oe 9.50 (s, 1H), 8.90 (d, 1H, J 5.2 Hz), 8.02 (d, 1H, J 5.2 Hz).
41% With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In toluene;Reflux; [00156j To a mixture of pyrido[3,4-d]pyridine-2,4(1H,3H)-dione (2 g, 12.3 mmol) in toluene (50 mL) was added DIEA (3.15 g, 25 mmol) and POC13 (9.5 g, 61.4 mmol). The reaction mixture was refluxed overnight. The solution was concentrated in vacuo and the residue was taken in ethyl acetate and washed with aq. NaHCO3 and brine. The organics were dried and concentrated. The residue was purified by silica gel chromatography (25percent EA:PE) to afford lg (4 1percent) of the title compound. ?H NMR (400 MHz, DMSO-d6): oe 9.50 (s, 1H), 8.90 (d, 1H, J 5.2Hz), 8.02 (d, 1H, J 5.2Hz).
  • 2
  • [ 7579-20-6 ]
  • [ 57-13-6 ]
  • [ 21038-67-5 ]
YieldReaction ConditionsOperation in experiment
78% In neat (no solvent); at 210℃; for 1h; A mixture of urea (40.00 g, 666.00 mmol) and 3-aminoisonicotinic acid (2a, 18.40 g, 133.20 mmol) was heated at 210°C for 1 hr (NOTE: no solvent was used). NaOH (2N, 320 mL) was added, and the mixture was stirred at 90°C for 1 h. The solid was collected by filtration, and washed with water. The crude product thus obtained was suspended in HOAc (400 mL), and stirred at 100°C for 1 h. The mixture was cooled to RT, filtered, and the solid was washed with a large amount of water, and then dried under the vacuum to give pyrido[3,4-d]pyrimidine-2,4(1 H,3H)-dione (2b, 17.00 g, 78percent yield) without further purification. LCMS (m/z [M+H]+): 164.0.
 

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