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Chemical Structure| 1225387-53-0 Chemical Structure| 1225387-53-0

Structure of 1225387-53-0

Chemical Structure| 1225387-53-0

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Product Details of [ 1225387-53-0 ]

CAS No. :1225387-53-0
Formula : C3H5N3
M.W : 83.09
SMILES Code : NC1=CC=NN1
MDL No. :MFCD31727672
InChI Key :JVVRJMXHNUAPHW-UHFFFAOYSA-N
Pubchem ID :74561

Safety of [ 1225387-53-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314-H317
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3267
Packing Group:

Application In Synthesis of [ 1225387-53-0 ]

* 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 [ 1225387-53-0 ]

[ 1225387-53-0 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 6283-81-4 ]
  • [ 1225387-53-0 ]
  • [ 89819-56-7 ]
  • 2
  • [ 34461-00-2 ]
  • [ 1225387-53-0 ]
  • [ 63572-73-6 ]
YieldReaction ConditionsOperation in experiment
84% In acetic acid; at 90℃; A suspension of lH-pyrazol-5-amine (0.804 g, 9.48 mmol) and sodium nitromalonaldehyde monohydrate (1.56 g, 9.96 mmol) in acetic acid (12 mL) was heated to 9O0C overnight. The reaction mixture was cooled to room temperature and poured into water (50 mL). The resulting solids were collected by filtration. The solids were washed with water (3 X 20 mL) and dried in vacuo to give 5-nitro-l H-pyrazolo [3 ,4-b]pyridine (1.40 g, 84%) as a solid.
84% In acetic acid; at 90℃; A suspension of lH-pyrazol-5 -amine (0.804 g, 9.48 mmol) and sodium nitromalonaldehyde monohydrate (1.56 g, 9.96 mmol) in acetic acid (12 mL) was heated to 90C overnight. The reaction mixture was cooled to room temperature and poured into water (50 mL). The resulting solids were collected by filtration. The solids were washed with water (3 X 20 mL) and dried in vacuo to give 5-nitro-lH-pyrazolo[3,4-b]pyridine (1.40 g, 84%) as a solid.
  • 3
  • [ 34461-00-2 ]
  • [ 1225387-53-0 ]
  • [ 63572-73-6 ]
  • [ 116835-08-6 ]
  • 4
  • [ 1001-26-9 ]
  • [ 1225387-53-0 ]
  • [ 29274-22-4 ]
YieldReaction ConditionsOperation in experiment
99% With caesium carbonate; In N,N-dimethyl-formamide; at 110℃;Inert atmosphere; The compound 5-aminopyrazole (5 g, 60 mmol)And <strong>[1001-26-9]ethyl 3-ethoxyacrylate</strong> (13 g, 90 mmol)Cesium carbonate (29 g, 90 mmol)Was mixed in 100 ml of N, N-dimethylformamide,The reaction was heated to 110 ° C overnight.Cooled to room temperature, diluted with 200 ml of water,Ether extraction (40 mL x 3), the aqueous phase was concentrated under reduced pressure,The residue was purified by silica gel column chromatography (DCM: MeOH = 10: 1)4H-pyrazolo [1,5-a] pyrimidin-5-one (8 g) in 99percent yield.
  • 5
  • [ 1001-26-9 ]
  • [ 1225387-53-0 ]
  • ethyl 3-[5-amino-3-(3-bromophenyl)-1H-pyrazol-1-yl]-3-ethoxypropanoate [ No CAS ]
  • 2-(3-bromophenyl)-7-ethoxy-6,7-dihydropyrazolo[1,5-a]pyrimidin-5(4H)-one [ No CAS ]
  • 6
  • [ 24424-99-5 ]
  • [ 1225387-53-0 ]
  • [ 952674-76-9 ]
YieldReaction ConditionsOperation in experiment
Treatment of commercially available aminopyrazole 1 with di-tert-butyl-dicarbonate affords compound 2. Oxidation of 2 with dibenzoyl peroxide and KOH (U.S. Pat. No. 4,945,166) produces 1-hydroxypyrazole 3. Reaction of 3 with methyl iodide and N,N-diisopropylethylamine gives 1-methoxypyrazole 4 (J. Org. Chem. 1995, 60, 4995). Nitrosation of 4 with isoamyl nitrite produces the nitroso compound 5. Hydrogenation of 5 with Pd/C under hydrogen gives compound 6. Deprotection of 6 with 2N-HCl in 1,4-dioxane results in the formation of 2-Methoxy-2H-pyrazole-3,4-diamine 7.
  • 7
  • [ 25007-54-9 ]
  • [ 1225387-53-0 ]
  • [ 1030018-65-5 ]
YieldReaction ConditionsOperation in experiment
32% In methanol; for 16h;Heating / reflux; Step A. <strong>[25007-54-9]Dimethyl 2-oxosuccinate</strong> (6.05 g, 37.8 mmol) and lH-pyrazol-3 -amine (3.14 g, 37.8 mmol) was heated to reflux in methanol (55 mL) for 16 h. After cooling down, the solid was collected by filtration and washed with methanol to afford methyl 7-hydroxypyrazolo[l,5-a]pyrimidine-5-carboxylate (2.32 g, 32%) as yellow solid. [MH]+ = 194.0.
  • 8
  • [ 1225387-53-0 ]
  • [ 934758-92-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; copper(l) chloride; isopentyl nitrite; In water; acetonitrile; at 0 - 20℃; for 180h;Inert atmosphere; To a souUon of 1H-pyrazo-5-amne (23.6 g, 284 mmo) n CH3CN (1 L) under a nitrogen atmosphere were added HC (140 m, 1420 mmo, 32%) and copper chorde (56.3 g, 568 mmo) at 0C, sopenty ntrte (80 mL 568 mmo) was added at 0C and the mixture was stirred at 0C for 2 days. sopenty nitrite (20 m, 0.5 eq) was added and the mixture was stirred at RT for another 5.5 days. The reaction mixture was sowy poured into ammonium hydroxide (1 L, 25%) and extracted with AcOEt. The organic phase was separated and the aqueous phase was extracted with AcOEt. The combined organic ayers were washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by sWca ge co?umn chromatography (hexane / TBME from 1:0 to 4:6) to afford 5-choro-1H-pyrazoe. Mz = 103/105 [M+H]+, Rt = 0.48 mm (UPLC Method B2), 1H NMR (600 MHz, DMSO-d6) : 6 ppm: 1300 (bs, IH), 7.79 (t, IH), 6.29 (t, IH), isoarny acoho :4.28 (t, IH), 3.41 (q, 2H), 1.30 (q, 2H), 0.85 (d, 6H).
  • 9
  • [ 20026-96-4 ]
  • [ 1225387-53-0 ]
  • 7-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5(4H)-one [ No CAS ]
 

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