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Chemical Structure| 7504-94-1 Chemical Structure| 7504-94-1

Structure of 7504-94-1

Chemical Structure| 7504-94-1

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Product Details of [ 7504-94-1 ]

CAS No. :7504-94-1
Formula : C4H6N4
M.W : 110.12
SMILES Code : NNC1=NC=CC=N1
MDL No. :MFCD01249337
InChI Key :QDGHXQFTWKRQTG-UHFFFAOYSA-N
Pubchem ID :346558

Safety of [ 7504-94-1 ]

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

Application In Synthesis of [ 7504-94-1 ]

* 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 [ 7504-94-1 ]

[ 7504-94-1 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 1722-12-9 ]
  • [ 7504-94-1 ]
YieldReaction ConditionsOperation in experiment
99.8% With potassium carbonate; hydrazine hydrate; at 100℃; for 0.5h; [1484] a mixture of 2-chloropyrimidine (15 g, 131 mmol), NH2NH2.H2O (30 ml), K2CO3 (15 g, 109 mmol) was stirred at 100 C for 30 min. The mixture was ice cooled and the resulting crude crystals were collected by filtration. The crystals were washed with cold water, air dried, and recrystallized from petroleum ether (150 ml) to give compound 350a (14.4 g, 131 mmol, yield: 99.8%) as a yellow solid. 1H NMR (400mhz, DMSO-d6) delta 8.30 (d, = 4.8 hz, 2h), 8.12 (br s, ih), 6.59 (t, j = 4.7 hz, ih), 4.13 (s, 2h).
87% With hydrazine hydrate; In ethanol;Reflux; General procedure: To 2-chloropyridine (1.1 mmol) in ethanol (5.0 mL) was added hydrazine hydrate (2 mL) dropwise at room temperature. The mixture was refluxed until completion as monitored by TLC. The reaction mixture was cooled, ethanol was removed by evaporation. Then, the residue was partitioned between ethyl acetate and water. The combined organic phase was dried over anhydrous sodium sulfate and concentrated to give the product, which was used for the following cyclization reaction without purification.
82% With potassium carbonate; hydrazine hydrate; Reference Example 2-57 2-Hydrazinopyrimidine The title compound was prepared according to the method described in Yakugaku Zasshi, vol.73, p.598 (1953). A mixture of 2-chloropyrimidine (25.0 g, 218 mmol), potassium carbonate (25.0 g, 181 mmol), and hydrazine monohydrate (50 mL, 1.01 mol) was heated and stirred at 100 C. for 20 minutes. The mixture was ice cooled and the resulting crude crystals were collected by filtration. The crystals were washed with cold water, air dried, and recrystallized from benzene to give the title compound (19.7 g, 82% yield). NMR (DMSO-d6) delta: 4.12 (2H, br s), 6.60 (1H, t, J=4.8 Hz), 8.10 (1H, br s), 8.31 (2H, d, J=4.8 Hz).
80% With hydrazine hydrate; In ethanol; for 2h; H2mphp was synthesized by the following procedure. 2-Chloropyrimidine (1.145 g, 20 mmol) was dissolvedin ethanol (30 mL). Then, excess hydrazine hydrate (85%, 6 mL) was added to the above solutionunder stirring. A bright yellow solution formed, from which white needle crystals appeared after 2 h. The crystals were collected by filtration and recrystallized in ethanol (yield 80%). 3-Methylsalicylaldehyde(1.36 g, 10 mmol) was added to an ethanolic solution (30 mL) of 2-hydrazinopyrimidine (1.10 g, 10 mmol)and light yellow precipitate formed immediately. After reflux for 3 h, the reaction mixture was filteredand the precipitate washed with ethanol to yield light yellow powder of H2mphp. Yield 95%.
40% With hydrazine; In ethanol; at 20℃; for 1.33333h; [Referential Example 34] 2-Hydrazinopyrimidine; [Show Image] Hydrazine monohydrate (20 ml) was added to a suspension of 2-chloropyrimidine (6.00 g) in ethanol (60 ml) at room temperature, and the mixture was stirred for 80 minutes. The solvent was evaporated under reduced pressure, and water (34 ml) was added to the residue. The solid precipitate was collected by filtration to give the title compound (2.30 g, 40%). 1H-NMR (400 MHz, DMSO-d6)delta: 4.12 (2H, s), 6.57-6.60 (1H, m), 8.12 (1H, s), 8.30 (2H, d, J = 4.9 Hz). EI-MSm/z: 110 (M+).
40% With hydrazine; In ethanol; at 20℃; for 1.33333h; [Referential Example 3] 2-Hydrazinopyrimidine [Show Image] Hydrazine monohydrate (20 mL) was added to a suspension of 2-chloropyrimidine (6.00 g) in ethanol (60 mL) at room temperature, followed by stirring for 80 minutes. The solvent of reaction mixture was evaporated under reduced pressure, and then water (34 mL) was added to the residue. The solid that precipitated was collected through filtration, to thereby give the title compound (2.30 g, 40%). 1H-NMR(400MHz,DMSO-d6)delta:4.12(2H,s), 6.57-6.60 (1H,m), 8.12(1H,s), 8.30(2H,d,J=4.9Hz). EI-MS m/z:110(M+).
25% With pyridine; hydrazine; at 20℃; for 1.6h; PREPARATION 9Preparation of 2-hydrazinylpyrimidine; A solution of 2-chloropyrimidine (0.70 g, 6.11 mmol) in pyridine (15 mL) and anhydrous hydrazine (2.5 mL) was stirred for 5 minutes at ambient temperature, and further pyridine (8 mL) was added. The reaction mixture was stirred at ambient temperature for 1.5 h and concentrated in vacuo. The residue was suspended in water (4 mL) and the resultant solid was collected by suction filtration and air-dried to afford 2-hydrazinylpyrimidine as a colorless solid in 25% yield (0.171 g): 1H NMR (300 MHz, DMSO-d6) delta 8.29 (d, J = 4.8 Hz, 2H), 8.13 (br s, 1 H), 6.59 (t, J = 4.8 Hz, 1 H), 4.12 (br s, 2H).
With hydrazine hydrate; In ethanol; Preparation Example 2 of Intermediate Compound Hydrazine monohydrate (43.5 g) was added to a solution of 2-chloropyrimidine (33 g) in ethanol, and the mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure, and the crystalline product thus obtained was recrystallized from ethyl acetate (50 ml) to give 2-hydrazinopyrimidine (20 g). Melting point 109.5C. 1H-NMR (CDCl3/DMSO-d6/TMS) delta (ppm): 8.34 (d, 2H), 6.38 (brs, 1H), 6.62 (t, 1H), 3.98 (brs, 2H).
With hydrazine hydrate; In methanol; at 10 - 40℃; for 1.5h; 1) Synthesis of compound B: A solution of 26.2 g of a hydrazine monohydrate (manufactured by Wako Pure Chemical Industries, Ltd.) and 30 mL of methanol was adjusted to an internal temperature of 10C, and 15 g of Compound (A) (manufactured by Wako Pure Chemical Industries, Ltd.) is gradually added thereto, followed by stirring for 0.5 hours at the same temperature. Then, an internal temperature was elevated to 40C, and the mixture was stirred for 1.0 hour. Subsequently, the reaction liquid was allowed to cool to room temperature, and 30 mL of water was added thereto, followed by filtration and washing with 30 mL of each of water and isopropyl alcohol. The resulting crystals were dried at room temperature for 8 hours to obtain 12.4 g of Compound (B). (1H-NMR(DMSO-d6), delta value TMS standard: 4.08 to 4.20(2H, brs), 6.55 to 6.72(2H, d), 8.10 to 8.15(1H, s), 8.27 to 8.35(2H, d))
With hydrazine hydrate; at 100℃; General procedure: A mixture of 2-chloro-5-methyl-benzimidazole (10.2 g, 61.2 mmol) and hydrazine monohydrate (59 mL, 1.22 mol) was stirred at 100 C overnight. After being cooled to ambient temperature, to the reaction mixture was added to water (60 mL). After stirring under ice cooling, the resulting precipitates were collected by filtration. The precipitates were washed with water 3 times, and then dried in vacuo to give 2-hydrazino-5-methyl-benzimidazole (8.4 g, 84.6%).
With hydrazine hydrate; In ethanol; at 60℃; General procedure: Hydrazine hydrate (5 mL) and 14a (10 mmol)was added to EtOH, and the mixture was heated to 60C overnight. After cooling, the solvent was evaporated, and the residue was diluted with 50 mL water, and extracted with DCM (50 mL×3). The combined organic extract was washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo to get the crude product 15a which was used in the next step without further purification. A solution of 2-hydroxybenzaldehyde (122 mg, 1 mmol) in 5 mL MeOH was added slowly to a solution of 15a (1 mmol), and the mixture was heated at 40C overnight. The residue was filtered, and washed with water, brine and petrol ether to give the product 16b.

  • 2
  • [ 931-63-5 ]
  • [ 7504-94-1 ]
  • 8
  • [ 7504-94-1 ]
  • [ 122-85-0 ]
  • acetic acid-[4-(pyrimidin-2-ylhydrazono-methyl)-anilide] [ No CAS ]
  • 11
  • [ 7504-94-1 ]
  • [ 56434-32-3 ]
  • (6<i>R</i>)-3-acetoxymethyl-8-oxo-7<i>t</i>-(3-pyrimidin-2-ylhydrazono-butyrylamino)-(6<i>r</i><i>H</i>)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid [ No CAS ]
  • 12
  • [ 7504-94-1 ]
  • [ 870-73-5 ]
  • [ 65267-32-5 ]
  • 13
  • [ 7504-94-1 ]
  • [ 80370-42-9 ]
  • ethyl 1-(2-pyrimidinyl)-1H-pyrazole-4-carboxylate [ No CAS ]
  • 14
  • [ 7504-94-1 ]
  • Toluene-4-sulfonate2-(4-formyl-phenyl)-1-methyl-imidazo[1,2-a]pyridin-1-ium; [ No CAS ]
  • [ 123510-68-9 ]
  • 15
  • [ 7504-94-1 ]
  • [ 4185-69-7 ]
  • (2,4-Dinitro-phenyl)-[(1Z,3Z)-5-(pyrimidin-2-yl-hydrazono)-penta-1,3-dienyl]-amine [ No CAS ]
  • 16
  • [ 7504-94-1 ]
  • [ 108967-20-0 ]
  • 3-β-D-nitrofuranosyl-1,2,4-triazolo<4,3-a>pyrimidine [ No CAS ]
  • 17
  • [ 7504-94-1 ]
  • [ 108967-20-0 ]
  • [ 123518-16-1 ]
  • 18
  • [ 7504-94-1 ]
  • [ 87-13-8 ]
  • [ 171193-36-5 ]
  • 19
  • [ 7504-94-1 ]
  • [ 1102-88-1 ]
  • 3-Digitoxigenone-2'-(pyrimidine-2''-yl) hydrazone nitrate [ No CAS ]
  • 20
  • [ 7504-94-1 ]
  • [ 26623-73-4 ]
  • (3S,5R,8R,9S,10S,13R,14S,17S)-10,13-Dimethyl-17-(pyrimidin-2-yl-hydrazonomethyl)-hexadecahydro-cyclopenta[a]phenanthrene-3,14-diol [ No CAS ]
  • 21
  • [ 7504-94-1 ]
  • [ 141-97-9 ]
  • 5-methyl-2-(pyrimidin-2-yl)-1H-pyrazol-3(2H)-one [ No CAS ]
  • 22
  • [ 7504-94-1 ]
  • [ 50-99-7 ]
  • (2R,3R,4R,5S)-6-(Pyrimidin-2-yl-hydrazono)-hexane-1,2,3,4,5-pentaol [ No CAS ]
  • 23
  • [ 7504-94-1 ]
  • [ 91-02-1 ]
  • N-[1-Phenyl-1-pyridin-2-yl-meth-(E)-ylidene]-N'-pyrimidin-2-yl-hydrazine [ No CAS ]
  • 24
  • [ 7504-94-1 ]
  • [ 600-22-6 ]
  • 2-(Pyrimidin-2-yl-hydrazono)-propionic acid methyl ester [ No CAS ]
  • 25
  • [ 7504-94-1 ]
  • [ 127-17-3 ]
  • 2-(Pyrimidin-2-yl-hydrazono)-propionic acid [ No CAS ]
  • 26
  • [ 7504-94-1 ]
  • [ 78-98-8 ]
  • C11H12N8 [ No CAS ]
  • 27
  • [ 7504-94-1 ]
  • [ 1620-98-0 ]
  • 2,6-di-tert-butyl-4-(pyrimidin-2-ylhydrazonomethyl)phenol [ No CAS ]
  • 28
  • [ 7504-94-1 ]
  • [ 149301-52-0 ]
  • 8-Cyclohexyl-2-pyrimidin-2-yl-2,5-dihydro-pyrazolo[4,3-c]quinolin-3-one [ No CAS ]
  • 29
  • [ 7504-94-1 ]
  • [ 149301-52-0 ]
  • 6-Cyclohexyl-4-(N'-pyrimidin-2-yl-hydrazino)-quinoline-3-carboxylic acid ethyl ester [ No CAS ]
  • 30
  • [ 7504-94-1 ]
  • [ 149301-53-1 ]
  • 8-Butyl-2-pyrimidin-2-yl-2,5-dihydro-pyrazolo[4,3-c]quinolin-3-one [ No CAS ]
  • 31
  • [ 7504-94-1 ]
  • [ 149301-53-1 ]
  • 6-Butyl-4-(N'-pyrimidin-2-yl-hydrazino)-quinoline-3-carboxylic acid ethyl ester [ No CAS ]
  • 32
  • [ 7504-94-1 ]
  • [ 150258-20-1 ]
  • 6,8-Difluoro-2-pyrimidin-2-yl-2,5-dihydro-pyrazolo[4,3-c]quinolin-3-one [ No CAS ]
  • 33
  • [ 7504-94-1 ]
  • [ 150258-20-1 ]
  • 6,8-Difluoro-4-(N'-pyrimidin-2-yl-hydrazino)-quinoline-3-carboxylic acid ethyl ester [ No CAS ]
  • 34
  • [ 7504-94-1 ]
  • 4-Chloro-5,6,7-trimethoxy-quinoline-3-carboxylic acid ethyl ester [ No CAS ]
  • 7,8,9-Trimethoxy-2-pyrimidin-2-yl-2,5-dihydro-pyrazolo[4,3-c]quinolin-3-one [ No CAS ]
  • 35
  • [ 7504-94-1 ]
  • [ 65-22-5 ]
  • (E)-5-(hydroxymethyl)-2-methyl-4-((2-(pyrimidin-2-yl)hydrazono)methyl)pyridin-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% In ethanol; at 20℃; General procedure: The desired compounds 1a-g and 2a-f were prepared by reaction between pyridoxal hydrochloride (0.15 g, 0.74mmol) and the appropriate aromatic or heteroaromatic hydrazine or N-acylhydrazine (1.1 eq., 0.81mmol) in ethanol (10.0 mL). The reaction mixture was stirred for 1-48 hours at room temperature. After that, product was purified by wash-ing with cold ethanol (3.0 mL) and cold diethyl ether (3.0 mL), leading to the pure derivatives 1a-g and 2a-f as solid in 42-86% yields.
 

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[ 7504-94-1 ]

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