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Structure of 143982-40-5

Chemical Structure| 143982-40-5

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Product Details of [ 143982-40-5 ]

CAS No. :143982-40-5
Formula : C7H5N3O
M.W : 147.13
SMILES Code : O=CC1=CN2C=CC=NC2=N1
MDL No. :MFCD09994887
InChI Key :BJPFFMZIQGNKKA-UHFFFAOYSA-N
Pubchem ID :15152331

Safety of [ 143982-40-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 143982-40-5 ]

* 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 [ 143982-40-5 ]

[ 143982-40-5 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 637-81-0 ]
  • [ 143982-40-5 ]
  • ethyl 2-azido-3-(imidazo<1,2-a>pyrimidin-2-yl)propenoate [ No CAS ]
  • 2
  • [ 143982-38-1 ]
  • [ 106012-56-0 ]
  • [ 143982-40-5 ]
  • 3
  • [ 637-81-0 ]
  • [ 143982-40-5 ]
  • (Z)-2-Azido-3-imidazo[1,2-a]pyrimidin-2-yl-acrylic acid ethyl ester [ No CAS ]
  • 4
  • [ 79-46-9 ]
  • [ 57892-71-4 ]
  • [ 106012-56-0 ]
  • [ 143982-40-5 ]
  • 2-(2-methyl 2-nitropropyl)imidazo<1,2-a>pyrimidine [ No CAS ]
  • 5
  • [ 57892-71-4 ]
  • [ 106012-56-0 ]
  • [ 143982-40-5 ]
  • 2-(2-methyl 2-nitropropyl)imidazo<1,2-a>pyrimidine [ No CAS ]
  • 6
  • [ 143982-40-5 ]
  • C29H25N4O2P [ No CAS ]
  • 7
  • [ 143982-40-5 ]
  • [ 143982-49-4 ]
  • 8
  • [ 3291-03-0 ]
  • [ 143982-40-5 ]
  • (E)-N'-((imidazo[1,2-a]pyrimidin-2-yl)methylene)-3,4,5-trimethoxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% In ethanol; for 1.0h;Reflux; General procedure: Aromatic/heteroaromatic aldehydes a-l(1.0 mmol) was added to ethanol (2 mL) containingcompound 3 (100 mg, 0.40 mmol) and heated toreux point for 1h. The solids obtained was flteredand slurred with ethanol (1mL) followed by n-Hexaneto get the hydrazones 4a-l .
  • 9
  • C7H7Cl2N3O*ClH [ No CAS ]
  • [ 143982-40-5 ]
  • 10
  • [ 143982-40-5 ]
  • C18H14N6O4 [ No CAS ]
  • 11
  • [ 143982-40-5 ]
  • dimethyl (1-cis,2-trans,3-cis)-3,4-bis(imidazo[1,2-a]pyrimidin-2-yl)cyclobutane-1,2-dicarboxylate [ No CAS ]
  • 12
  • [ 143982-40-5 ]
  • (1-trans,2-trans,3-trans)-3,4-bis(imidazo[1,2-a]pyrimidin-2-yl)cyclobutane-1,2-dicarboxylic acid [ No CAS ]
  • 13
  • [ 143982-40-5 ]
  • dimethyl (1-trans,2-trans,3-trans)-3,4-bis(imidazo[1,2-a]pyrimidin-2-yl)cyclobutane-1,2-dicarboxylate [ No CAS ]
  • 14
  • [ 143982-40-5 ]
  • C20H16N6O4 [ No CAS ]
  • 15
  • [ 141-82-2 ]
  • [ 143982-40-5 ]
  • (E)-3-(imidazo[1,2-a]pyrimidin-2-yl)acrylic acid [ No CAS ]
  • 16
  • [ 536-40-3 ]
  • [ 143982-40-5 ]
  • 4-chloro-N'-((imidazo[1,2-a]pyrimidin-2-yl)methylene) benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% In ethanol; for 5.0h;Reflux; General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds.
  • 17
  • [ 31822-03-4 ]
  • [ 143982-40-5 ]
  • N'-((imidazo[1,2-a] pyrimidin-2-yl )methylene)-2-iodobenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In ethanol; for 5.0h;Reflux; General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds.
  • 18
  • [ 3291-03-0 ]
  • [ 143982-40-5 ]
  • N'-((imidazo[1,2-a] pyrimidin-2-yl)methylene)-3,4,5-trimethoxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% In ethanol; for 5.0h;Reflux; General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds.
  • 19
  • [ 143982-40-5 ]
  • [ 618-94-0 ]
  • N'-((imidazo[1,2-a]pyrimidin-2-yl)methylene)-3-nitrobenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In ethanol; for 5.0h;Reflux; General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds.
  • 20
  • [ 143982-40-5 ]
  • [ 5933-32-4 ]
  • 4-bromo-N'-((imidazo[1,2-a]pyrimidin-2-yl)methylene)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% In ethanol; for 5.0h;Reflux; General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds.
  • 21
  • [ 29418-67-5 ]
  • [ 143982-40-5 ]
  • 2-bromo-N'-((imidazo[1,2-a]pyrimidin-2-yl)methylene)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% In ethanol; for 5.0h;Reflux; General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds.
  • 22
  • [ 5351-23-5 ]
  • [ 143982-40-5 ]
  • 4-hydroxy-N'-((imidazo[1,2-a] pyrimidin-2-yl)methylene)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% In ethanol; for 5.0h;Reflux; General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds.
  • 23
  • [ 613-94-5 ]
  • [ 143982-40-5 ]
  • N'-((Imidazo[1,2-a]pyrimidin-2-yl)methylene)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% In ethanol; for 5.0h;Reflux; General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds.
  • 24
  • [ 456-06-4 ]
  • [ 143982-40-5 ]
  • 4-fluoro-N'-((imidazo[1,2-a]pyrimidin-2-yl)methylene)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% In ethanol; for 5.0h;Reflux; General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds.
  • 25
  • [ 53554-94-2 ]
  • [ 143982-40-5 ]
  • N'-((imidazo[1,2-a]pyrimidin-2-yl)methylene)4(methylsulfonyl)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% In ethanol; for 5.0h;Reflux; General procedure: To a stirred solution of compound 3 (100 mg, 0.30 mmol) in ethanol was added corresponding benzohydrazides (1.0 mmol) and refluxed for 5 h. The reaction medium was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure, to obtain the pure compounds.
  • 26
  • [ 143982-38-1 ]
  • [ 143982-40-5 ]
YieldReaction ConditionsOperation in experiment
60% With calcium carbonate; In water; for 1.0h;Reflux; A mixture of compound 2 (1g, 4.95 mmol), CaCO3 (5g, 24.75 mmol) in water (30 mL) was refluxed for 1h. The reaction mixture was cooled to room temperature and extracted with ethylacetate and evaporated under reduced pressure to obtain the crude compound 3, which was purified by columnchromatography (silica gel: 60 - 120 mesh, eluent: 1% MeOH / CHCl3) to afford compound 3. Pale yellow solid, Yield: 60%; M.p: 209 - 210oC. IR (KBr): νmax 2934 (C-H aromatic), 1644 (C=O), 1543 (C=N),1213(C-N) cm-1; 1H NMR (400 MHz, CDCl3): d 9.96 (s, 1H), 9.66 (q, J = 6.8 Hz, 1H), 8.88 (q, J = 4.0 Hz,1 H), 8.70 (s, 1H), 7.43 (q, J = 6.4 Hz, 1 H). ESI-MS:m/z (rel.abund.%) 148.2 (M+H). [Found: C, 56.58; H,2.83.21; N, 27.98 C7H5N3O requires C, 57.14; H, 3.43;N, 28.56].
  • 27
  • [ 126-81-8 ]
  • [ 143982-40-5 ]
  • [ 109-77-3 ]
  • 2‑amino‑4‑(imidazo[1,2‑a]pyrimidin‑2‑yl)‑7,7‑dimethyl‑5‑oxo‑5,6,7,8‑tetrahydro‑4H‑chromene‑3‑carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With sodium carbonate; In ethanol; water; at 25.0℃; for 3.0h; General procedure: Imidazo[1,2-a]pyrimidine-2-carbaldehyde [40] (100 mg,0.68 mmol, 1.0 equiv.), 58 mg malononitrile (0.88 mmol, 1.3equiv.), and enolizable compounds (0.88 mmol, 1.3 equiv.)were dissolved in 5 cm3water or a mixture of water:ethylalcohol (4:1). Sodium carbonate (0.88 mmol, 93 mg, 1.3equiv.) in 2 cm3water was added and the mixture was stirredat room temperature for various times (2-7 h). The reactionprocess was monitored with thin layer chromatographyusing different ratio of hexane:ethyl acetate mixture assolvent. After completion of the reaction, the mixture waspoured into brine solution and stirred for 15 min. The resultingsolid was suction filtered using filter paper with smallpore size and washed with water. The pure products 4a-4gwere obtained by crystallization or washing with varioussolvents. Products were stored under argon atmosphere toprevent decomposition.
  • 28
  • [ 143982-40-5 ]
  • [ 109-77-3 ]
  • [ 108-46-3 ]
  • 2‑amino‑7‑hydroxy‑4‑(imidazo[1,2‑a]pyrimidin‑2‑yl)‑4H‑chromene‑3‑carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With sodium carbonate; In water; at 25.0℃; for 2.0h; General procedure: Imidazo[1,2-a]pyrimidine-2-carbaldehyde [40] (100 mg,0.68 mmol, 1.0 equiv.), 58 mg malononitrile (0.88 mmol, 1.3equiv.), and enolizable compounds (0.88 mmol, 1.3 equiv.)were dissolved in 5 cm3water or a mixture of water:ethylalcohol (4:1). Sodium carbonate (0.88 mmol, 93 mg, 1.3equiv.) in 2 cm3water was added and the mixture was stirredat room temperature for various times (2-7 h). The reactionprocess was monitored with thin layer chromatographyusing different ratio of hexane:ethyl acetate mixture assolvent. After completion of the reaction, the mixture waspoured into brine solution and stirred for 15 min. The resultingsolid was suction filtered using filter paper with smallpore size and washed with water. The pure products 4a-4gwere obtained by crystallization or washing with varioussolvents. Products were stored under argon atmosphere toprevent decomposition.2-Amino-7-hydrox y-4- ( imidazo[1,2- a ]pyr imi -din-2-yl)-4H-chromene-3-carbonitrile (4a, C16H11N5O2)Usingresorcinol in water with 2 h reaction time. The pure product4a was obtained by crystallization with toluene/ethyl alcohol.Cream-colored solid; yield: 0.17 g (83%); m.p.: > 300 C(dec.); 1H NMR (600 MHz, DMSO-d6): δ = 9.86 (1H, s), 8.52(1H, dd, J = 3.90, 1.89 Hz), 8.48 (1H, dd, J = 6.88, 1.61 Hz),7.63 (1H, s), 7.11 (2H, s), 7.04 (1H, dd, J = 4.1, 2.73 Hz),6.73 (1H, t, J = 4.55 Hz), 6.46 (2H, m), 5.41 (1H, s) ppm;13C NMR (150 MHz, DMSO-d6): δ = 161.41, 158.20, 150.00,149.81, 148.58, 134.00, 132.59, 129.27, 125.14, 120.40,113.17, 109.90, 109.23, 103.04, 52.30, 30.56 ppm; IR (ATR): v = 3477, 3384, 3337, 3187, 3094, 2990, 2919, 2185, 1651,1617, 1592, 1497, 1398, 1318, 1279, 1139, 1111, 1037, 911,874, 839, 788, 773, 699, 667 cm-1; MS: m/z (%) = 306 (M+,100), 279 (40), 206 (36), 180 (36).
  • 29
  • [ 143982-40-5 ]
  • [ 591-27-5 ]
  • [ 109-77-3 ]
  • 2,7‑diamino‑4‑(imidazo[1,2‑a]pyrimidin‑2‑yl)‑4H‑chromene‑3‑carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With sodium carbonate; In ethanol; water; at 25.0℃; for 5.0h; General procedure: Imidazo[1,2-a]pyrimidine-2-carbaldehyde [40] (100 mg,0.68 mmol, 1.0 equiv.), 58 mg malononitrile (0.88 mmol, 1.3equiv.), and enolizable compounds (0.88 mmol, 1.3 equiv.)were dissolved in 5 cm3water or a mixture of water:ethylalcohol (4:1). Sodium carbonate (0.88 mmol, 93 mg, 1.3equiv.) in 2 cm3water was added and the mixture was stirredat room temperature for various times (2-7 h). The reactionprocess was monitored with thin layer chromatographyusing different ratio of hexane:ethyl acetate mixture assolvent. After completion of the reaction, the mixture waspoured into brine solution and stirred for 15 min. The resultingsolid was suction filtered using filter paper with smallpore size and washed with water. The pure products 4a-4gwere obtained by crystallization or washing with varioussolvents. Products were stored under argon atmosphere toprevent decomposition.
  • 30
  • [ 504-15-4 ]
  • [ 143982-40-5 ]
  • [ 109-77-3 ]
  • 2‑amino‑7‑hydroxy‑4‑(imidazo[1,2‑a]pyrimidin‑2‑yl)‑5‑methyl‑4H‑chromene‑3‑carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With sodium carbonate; In water; at 25.0℃; for 2.0h; General procedure: Imidazo[1,2-a]pyrimidine-2-carbaldehyde [40] (100 mg,0.68 mmol, 1.0 equiv.), 58 mg malononitrile (0.88 mmol, 1.3equiv.), and enolizable compounds (0.88 mmol, 1.3 equiv.)were dissolved in 5 cm3water or a mixture of water:ethylalcohol (4:1). Sodium carbonate (0.88 mmol, 93 mg, 1.3equiv.) in 2 cm3water was added and the mixture was stirredat room temperature for various times (2-7 h). The reactionprocess was monitored with thin layer chromatographyusing different ratio of hexane:ethyl acetate mixture assolvent. After completion of the reaction, the mixture waspoured into brine solution and stirred for 15 min. The resultingsolid was suction filtered using filter paper with smallpore size and washed with water. The pure products 4a-4gwere obtained by crystallization or washing with varioussolvents. Products were stored under argon atmosphere toprevent decomposition.
  • 31
  • [ 95-88-5 ]
  • [ 143982-40-5 ]
  • [ 109-77-3 ]
  • 2‑amino‑6‑chloro‑7‑hydroxy‑4‑(imidazo[1,2‑a]pyrimidin‑2‑yl)‑4H‑chromene‑3‑carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With sodium carbonate; In ethanol; water; at 25.0℃; for 2.0h; General procedure: Imidazo[1,2-a]pyrimidine-2-carbaldehyde [40] (100 mg,0.68 mmol, 1.0 equiv.), 58 mg malononitrile (0.88 mmol, 1.3equiv.), and enolizable compounds (0.88 mmol, 1.3 equiv.)were dissolved in 5 cm3water or a mixture of water:ethylalcohol (4:1). Sodium carbonate (0.88 mmol, 93 mg, 1.3equiv.) in 2 cm3water was added and the mixture was stirredat room temperature for various times (2-7 h). The reactionprocess was monitored with thin layer chromatographyusing different ratio of hexane:ethyl acetate mixture assolvent. After completion of the reaction, the mixture waspoured into brine solution and stirred for 15 min. The resultingsolid was suction filtered using filter paper with smallpore size and washed with water. The pure products 4a-4gwere obtained by crystallization or washing with varioussolvents. Products were stored under argon atmosphere toprevent decomposition.
  • 32
  • [ 143982-40-5 ]
  • [ 109-77-3 ]
  • [ 87-66-1 ]
  • 2‑amino‑7,8‑dihydroxy‑4‑(imidazo[1,2‑a]pyrimidin‑2‑yl)‑4H‑chromene‑3‑carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With sodium carbonate; In water; at 25.0℃; for 2.0h; General procedure: Imidazo[1,2-a]pyrimidine-2-carbaldehyde [40] (100 mg,0.68 mmol, 1.0 equiv.), 58 mg malononitrile (0.88 mmol, 1.3equiv.), and enolizable compounds (0.88 mmol, 1.3 equiv.)were dissolved in 5 cm3water or a mixture of water:ethylalcohol (4:1). Sodium carbonate (0.88 mmol, 93 mg, 1.3equiv.) in 2 cm3water was added and the mixture was stirredat room temperature for various times (2-7 h). The reactionprocess was monitored with thin layer chromatographyusing different ratio of hexane:ethyl acetate mixture assolvent. After completion of the reaction, the mixture waspoured into brine solution and stirred for 15 min. The resultingsolid was suction filtered using filter paper with smallpore size and washed with water. The pure products 4a-4gwere obtained by crystallization or washing with varioussolvents. Products were stored under argon atmosphere toprevent decomposition.
  • 33
  • [ 90-15-3 ]
  • [ 143982-40-5 ]
  • [ 109-77-3 ]
  • 2‑amino‑4‑(imidazo[1,2‑a]pyrimidin‑2‑yl)‑4H‑benzo[h]-chromene‑3‑carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With sodium carbonate; In ethanol; water; at 25.0℃; for 7.0h; General procedure: Imidazo[1,2-a]pyrimidine-2-carbaldehyde [40] (100 mg,0.68 mmol, 1.0 equiv.), 58 mg malononitrile (0.88 mmol, 1.3equiv.), and enolizable compounds (0.88 mmol, 1.3 equiv.)were dissolved in 5 cm3water or a mixture of water:ethylalcohol (4:1). Sodium carbonate (0.88 mmol, 93 mg, 1.3equiv.) in 2 cm3water was added and the mixture was stirredat room temperature for various times (2-7 h). The reactionprocess was monitored with thin layer chromatographyusing different ratio of hexane:ethyl acetate mixture assolvent. After completion of the reaction, the mixture waspoured into brine solution and stirred for 15 min. The resultingsolid was suction filtered using filter paper with smallpore size and washed with water. The pure products 4a-4gwere obtained by crystallization or washing with varioussolvents. Products were stored under argon atmosphere toprevent decomposition.
  • 34
  • [ 143982-40-5 ]
  • 2-(1-ethyl-4,5-diphenyl-1H-imidazol-2-yl)imidazo[1,2-a]pyrimidine [ No CAS ]
  • 35
  • [ 143982-40-5 ]
  • [ 62-53-3 ]
  • 2-(1,4,5-triphenyl-1H-imidazol-2-yl)imidazo[1,2-a]pyrimidine [ No CAS ]
 

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Technical Information

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