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Chemical Structure| 1393179-35-5 Chemical Structure| 1393179-35-5

Structure of 1393179-35-5

Chemical Structure| 1393179-35-5

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Product Details of [ 1393179-35-5 ]

CAS No. :1393179-35-5
Formula : C5H3ClN4
M.W : 154.56
SMILES Code : N#CC1=CN=C(N)N=C1Cl
MDL No. :MFCD27923125
InChI Key :UPUMETVQYQSNGW-UHFFFAOYSA-N
Pubchem ID :71741379

Safety of [ 1393179-35-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P280-P305+P351+P338-P310

Application In Synthesis of [ 1393179-35-5 ]

* 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 [ 1393179-35-5 ]

[ 1393179-35-5 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 3177-24-0 ]
  • [ 1393179-35-5 ]
YieldReaction ConditionsOperation in experiment
56% With ammonia; In 1,4-dioxane; at 20℃; for 4h; PREPARATION 972-Amino-4-chloropyrimidine-5-carbonitrileTo a solution of 2,4-dichloropyrimidine-5-carbonitrile (600mg, 3.45mmol) in dioxane (20ml) was added a 0.5M solution of NH3 in dioxane (20ml, 10 mmol) and the mixture stirred at room temperature for 4h. A mixture of two isomers were obtained and separated by column chromatography using a mixture of hexane/ethyl acetate (from 0percent to 45percent of ethyl acetate). The title compound (304mg, 56percent yield) was found to be the less polar isomer.LRMS (m/z): 153 (M-1 )\\
  • 2
  • [ 3177-24-0 ]
  • [ 1393179-35-5 ]
  • [ 94741-69-2 ]
YieldReaction ConditionsOperation in experiment
With ammonium hydroxide; In 1,4-dioxane; at 0 - 20℃; for 2h; Method E [0724] General conditions for the preparation of 2-amino-4-chloropyrimidine-5-carbonitrile: [0725] To a solution of 2,4-dichloropyrimidine-5-carbonitrile (E-1) (2.0 g, 11.5 mmol) in   1,4-dioxane (20 mL) at 0° C.,   ammonium hydroxide (28-30percent, 4.4 mL, 34.5 mmol) is added dropwise, and the resulting mixture is stirred while warming from 0° C. to RT for 2 h. Then, the mixture is partitioned between ethyl acetate (200 mL) and water (50 mL). The organic layer is washed with brine, dried over Na2SO4 and filtered. The filtrate is mixed with silica gel and then concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0-100percent ethyl acetate/hexanes to afford the product (   E-2) (917 mg) and a mixture of (E-2) and (E-3). Additional (E-3) can be obtained from this mixture by a second column chromatographic purification.
917 mg With ammonium hydroxide; In 1,4-dioxane; at 0 - 20℃; for 2h; [00607] General conditions for the preparation of 2-amino-4-chloropyrimidine-5-carbonitrile:[00608] To a solution of 2,4-dichloropyrimidine-5-carbonitrile (E-1) (2.0 g, 11.5 mmol) in 1,4-dioxane (20 mL) at 0 °C, ammonium hydroxide (28-30percent, 4.4 mL, 34.5 mmol) is added dropwise, and the resulting mixture is stirred while warming from 0 °C to RT for 2 h. Then, the mixture is partitioned between ethyl acetate (200 mL) and water (50 mL). The organic layer is washed with brine, dried over Na2SO4 and filtered. The filtrate is mixed with silica gel and then concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0- 100percent ethyl acetate/hexanes to afford the product (E-2) (917 mg) and a mixture of (E-2) and (E-3). Additional (E-3) can be obtained from this mixture by a second column chromatographic purification.
  • 3
  • [ 1393179-35-5 ]
  • [ 1425044-93-4 ]
  • [ 1425043-06-6 ]
YieldReaction ConditionsOperation in experiment
[0956] A solution of compound 195 (25 mg, 0.05 mmol, 1 equiv.) in 2 mL DCM at 22 C. was treated with two portions of TFA (2×80 uL, 2×1 mmol, 40 equiv) for one hour each. The mixture was concentrated in vacuo, co-evaporated with 10 mL DCM and then 10 mL hexanes. The residue was dissolved in 1 mL NMP, and N,N-diisopropylethylamine (20 muL, 2 equiv.) was added followed by <strong>[1393179-35-5]2-amino-4-chloro-5-cyanopyrimidine</strong>. The mixture was heated in a sealed tube at 110 C. for 15 h, cooled and treated with TBAF (2×200 muL, 1.0 M in THF, 0.4 mmol, 8 equiv.) and stirred for 4.5 h. The mixture was diluted with water (10 mL), and extracted with DCM (5×5 mL). The combined organic layers were washed with 10 mL brine, dried over sodium sulfate, filtered, and the solvent was removed in vacuo. The residue was purified by preparative HPLC to give compound 196. ESI-MS 450.2 [M+H]+.
  • 4
  • [ 1393179-35-5 ]
  • [ 1425045-77-7 ]
  • [ 1425042-18-7 ]
YieldReaction ConditionsOperation in experiment
10686] Step 2:10687] An appropriately sized reaction vessel wasequipped with mechanical stirrer, reflux condenser, temperature probe and inert gas inlet/outlet. The solution of Compound 3 (10 vol. based on Compound 2, 1 equiv.) from the previous step was charged to the vessel under an inert atmosphere. The thnnel and port were rinsed with 1 -butanol (0.5 volumes). The mixture was stirred at 20±5 C. 2-Amino-4- chloro-5-cyanopyrimidine (1.2 equiv.) was charged through a solid charge port under an inert atmosphere with stirring. N,N-Diisopropylethylamine (1.5 equiv.) was charged through the same charge port to the white suspension. The reaction mixture was heated to 90±5 C. (target temperature 89-91 C.) with stirring under argon. Afier the reaction was found to be complete (1 .0% Compound 3 relative to Compound 1 as determined by HPLC), the reaction mixture was cooled down to 20±5 C. over approximately 2 hrs. The agitation was slowed down to minimize crystal attrition. Upon reaching 20±5 C., the suspension was aged for 6 hours. Where the product didn?t nucleated upon reaching room temperature, the mixture was stirred at 20±5 C. until solid was observed then the batch was aged for a minimum of 6 hours. Potential hold point for up to 2 days at 20±5 C. The solid was filtered and the wet cake was washed with methyl tert-butyl ether (MTBE) (2x3 vol. with respect to the substrate). The solid was dried on the filter under vacuum for at least one hour, turned over regularly to help evenly dry the solid. The solid was transferred to a vacuum oven and dried at 40±5 C. under vacuum with nitrogen bleed until constant weight was achieved. Crude Compound 1 was collected as a pale yellow solid (1.48 kg, yield: .-90%).
  • 5
  • [ 1393179-35-5 ]
  • tert-butyl (S)-2-(5-chloro-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazine-2-yl)pyrrolidine- 1-carboxylate [ No CAS ]
  • [ 1549737-13-4 ]
  • 6
  • [ 1393179-35-5 ]
  • [ 1548343-96-9 ]
  • [ 1549737-54-3 ]
 

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