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[ CAS No. 114834-02-5 ]

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Chemical Structure| 114834-02-5
Chemical Structure| 114834-02-5
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Product Details of [ 114834-02-5 ]

CAS No. :114834-02-5 MDL No. :MFCD01631197
Formula : C7H5ClN4 Boiling Point : 371.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :180.59 g/mol Pubchem ID :-
Synonyms :

Safety of [ 114834-02-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 114834-02-5 ]

  • Downstream synthetic route of [ 114834-02-5 ]

[ 114834-02-5 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 123-75-1 ]
  • [ 114834-02-5 ]
  • 4-Imidazol-1-yl-6-pyrrolidin-1-yl-pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In acetone for 0.5h; Heating;
  • 2
  • [ 110-89-4 ]
  • [ 114834-02-5 ]
  • 4-(1H-imidazol-1-yl)-6-(piperidin-1-yl)pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% In acetone for 0.5h; Heating;
  • 3
  • [ 110-91-8 ]
  • [ 114834-02-5 ]
  • 4-(6-Imidazol-1-yl-pyrimidin-4-yl)-morpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% In acetone for 0.5h; Heating;
  • 4
  • [ 288-32-4 ]
  • [ 1193-21-1 ]
  • [ 114834-02-5 ]
  • 4,6-di(1H-imidazol-1-yl)pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride 1.) THF, RT, 20 min, 2.) THF, RT, overnight; Yield given. Multistep reaction. Yields of byproduct given;
  • 5
  • [ 92-54-6 ]
  • [ 114834-02-5 ]
  • 4-Imidazol-1-yl-6-(4-phenyl-piperazin-1-yl)-pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% In acetone for 0.5h; Heating;
  • 6
  • [ 124-41-4 ]
  • [ 114834-02-5 ]
  • 4-(1-imidazolyl)-6-methoxypyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% In methanol Ambient temperature;
  • 7
  • [ 114834-02-5 ]
  • [ 5188-07-8 ]
  • 4-methylthio-6-(1H-imidazol-1-yl)pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% In water; acetone for 2h; Ambient temperature;
  • 8
  • [ 141-52-6 ]
  • [ 114834-02-5 ]
  • 4-Ethoxy-6-imidazol-1-yl-pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% In ethanol Ambient temperature;
  • 9
  • [ 114834-02-5 ]
  • [pyrimidin-4-yl]-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With hydrogen; sodium acetate In methanol Ambient temperature;
  • 10
  • [ 114834-02-5 ]
  • [ 108-95-2 ]
  • 4-Imidazol-1-yl-6-phenoxy-pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene for 7h; Heating;
  • 11
  • [ 288-32-4 ]
  • [ 1193-21-1 ]
  • [ 114834-02-5 ]
YieldReaction ConditionsOperation in experiment
73% Stage #1: 1H-imidazole With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 4,6-dichloropyrimidine In N,N-dimethyl-formamide at 20℃; for 15h; 17 General procedure for the preparation of chloro-pyrrolo and chloro-imidazolodiazines 3m, 3n, 5m, 5n, 9m, 9n General procedure: To a solution pyrrole or imidazole (8.05 mmol) in DMF (10 mL) in a 50 mL round-bottom flask was added sodium hydride (8.86 mmol of NaH 60% dispersion in mineral oil). The mixture was stirred for 5 min at room temperature (H2 evolution). This solution was then transferred dropwise via a syringe to another 50 mL round-bottom flask containing dichlorodiazine (1.00 g, 6.71 mmol) in DMF (5 mL), and the resulting solution was stirred at room temperature (except for 3,6-dichloropyridazine and imidazole at 80 C). The reaction was monitored by GC. Once the starting dichlorodiazine was completely consumed, the mixture was poured into a saturated NH4Cl solution (30 mL) and extracted with CH2Cl2 (330 mL). The combined organic layers were dried over Na2SO4, filtered, and evaporated under vacuum. The crude product was purified by flash chromatography (elution with petroleum ether/acetone 95/5 to 80/20) to afford the pure product.
63% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; 347.A Step A: 4-Chloro-6-(1H-imidazol-1-yl)pyrimidine A mixture of 4,6-dichloropyrimidine (5.96 g, 40mmol), imidazole (2.72 g, 40.0 mmol), and potassium carbonate(5.53 g, 40.0 mmol) was stirred in DMF (50 mL) atroom temperature for 18 h. The reaction was diluted into 500mL water and extracted five times with 150 mL EtOAc. Thecombined organic layers were concentrated and purified byflash chromatography on a 240 g silica gel cartridge with 0 to10% methanol in ethyl acetate to yield 4-chloro-6-(lH-imidazol-1-yl)pyrimidine (4.56 g, 63% yield).
58% With potassium carbonate In N,N-dimethyl-formamide for 18h;
In water; N,N-dimethyl-formamide 3 EXAMPLE 3 EXAMPLE 3 This Example illustrates the preparation of (E)-methyl 2-[2-(6-(imidazol-1-yl)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (Compound No. 8 of Table I). To a stirred suspension of sodium hydride (0.65g, 55% dispersion in oil, pre-washed with petrol) in dry DMF (5ml) at 10-15° C under nitrogen, was added a solution of imidazole (1.02g, 15 mmol) over five minutes. The reaction mixture effervesced and an exotherm took place. After stirring for 11/2hours at room temperature, the cloudy solution was added drop-wise over one hour to a solution of 4,6-dichloropyrimidine in dry DMF (10ml) at 0° C. for one hour, added to water and then extracted with ether (*3). The combined ether extracts were washed with dilute sodium hydroxide solution and water (*3) and then dried. Concentration under reduced pressure gave 4-chloro-6-(imidazol-1-yl)pyrimidine as a pale yellow solid (1.00g); m.p. 122-4° C., which was used without further purification.
In tetrahydrofuran 12 6-Chloro-4-(1-imidazolyl)pyrimidine EXAMPLE 12 6-Chloro-4-(1-imidazolyl)pyrimidine In anhydrous tetrahydrofuran, 298 mg of 4,6-dichloro-pyrimidine was substituted with 136 mg of imidazole. The reaction mixture was treated according to the procedure of Example 5 to yield 283 mg of the 6-chloro-4-(1-imidazolyl)pyrimidine, recrystallized from a mixture of n-hexane and ethyl acetate, having a melting point of 131.5°-132° C. NMR(CDCl3)δ: 7.2-7.4(1H,m), 7.43(1H,s), 7.6-7.9(1H,m), 8.47(1H,s), 8.89(1H,s).

  • 12
  • sodium thiomethoxide [ No CAS ]
  • [ 114834-02-5 ]
  • 4-(imidazol-1-yl)-6-thiomethoxypyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide 3 EXAMPLE 3 A solution of 4-chloro-6-(imidazol-1-yl)pyrimidine (0.54g, 3 mmol) in dry DMF (5ml) was added drop-wise over five minutes to sodium thiomethoxide (0.23g, 3.15 mmol) in dry DMF (5ml) at 0° C. under nitrogen. After stirring at 0° C. for 45 minutes, the reaction mixture was allowed to warm to room temperature. After two hours, the reaction mixture was poured into water and extracted with ether (*3). The combined ether extracts were washed with water, dried and evaporated to give a pale yellow solid (0.30g). Chromatography on silicagel (eluent ether) afforded 4-(imidazol-1-yl)-6-thiomethoxypyrimidine (0.08g) as a white solid, m.p. 123-5° C. A second fraction (0.14g) containing 88% of the desired product as a white solid was also isolated.
  • 13
  • [ 696-62-8 ]
  • [ 114834-02-5 ]
  • [ 1312164-83-2 ]
YieldReaction ConditionsOperation in experiment
36% With (2,2'-bipyridine)nickel(II) dibromide; tetrabutylammomium bromide; ethylene dibromide In N,N-dimethyl-formamide at 20℃; for 4.5h; Inert atmosphere; Electrochemical reaction;
  • 14
  • [ 6077-72-1 ]
  • [ 114834-02-5 ]
  • [ 1372626-20-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-methylcyclopropanemethanol With sodium hydride In tetrahydrofuran; mineral oil for 1h; Stage #2: 4-chloro-6-(imidazol-1-yl)pyrimidine In tetrahydrofuran; mineral oil at 20℃; for 24h; 2 To a mixture of 0.26 g of. 2-methylcyclopropylmethanol and 10 mL of tetrahydrofuran was added 0.12 g of 60 % sodium hydride (in oil), and the mixture was stirred for 1 hour. To the/reaction mixture was added 0.5 g of 4-chloro- 6-imidazolylpyrimidine , and the mixture was stirred for 1 day at room temperature. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to obtain 0.34 g of Compound 3:
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