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Chemical Structure| 674793-32-9 Chemical Structure| 674793-32-9

Structure of 674793-32-9

Chemical Structure| 674793-32-9

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Product Details of [ 674793-32-9 ]

CAS No. :674793-32-9
Formula : C7H6ClFN2
M.W : 172.59
SMILES Code : NC(=N)C1=C(F)C=CC(Cl)=C1
MDL No. :MFCD09745080

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Application In Synthesis of [ 674793-32-9 ]

* 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 [ 674793-32-9 ]

[ 674793-32-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 674793-32-9 ]
  • [ 57595-23-0 ]
  • [ 773140-30-0 ]
YieldReaction ConditionsOperation in experiment
30% In ethanol; at 80℃; To a suspension of 4-oxo-tetrahydroiuran-3-carboxylic acid methyl ester (prepared according to Dowd, P.; Choi, S-C. Tetrahedron, 1991, 47, 4847-4860; 800 mg, EPO <DP n="60"/>5.55 mmol, leq) in ethanol (20 ml) was added a solution of 2-fluoro-5-chloro- benzamidine (961 mg, 5.55 mmol, 1 eq) in EtOH (10 ml). The reaction mixture was heated to 80C overnight. The reaction mixture was cooled to r.t. and the white precipitate was filtered and washed with cold ethyl actetate (2 x 20 ml). The crude residue was partitioned between chloroform and water. The aqueous layer was acidified to pH 4 and the product was extracted with chloroform (3 x 50 ml). The organic layers were combined, washed with brine, dried over MgSO4, filtered and concentrated in vacuo to give a crude solid which was purified by flash column chromatography (5% MeOH in EtOAc) to give a white solid 2-(5-chloro-2-fluoro- phenyl)-5,7-dihydrofuro[3,4-d]pyrimidin-4-ol (440mg, 30%)
  • 2
  • [ 674793-32-9 ]
  • [ 71486-53-8 ]
  • [ 773140-01-5 ]
YieldReaction ConditionsOperation in experiment
76% With sodium ethanolate; In ethanol; at 70℃; for 2h; To a solution of 2-fluoro-5-chlorobenzamidine (1.79 g, 10.4 mmol, 1 eq) in EtOH (10 ml) was added solid NaOEt (705 mg, 10.4 mmol, 1 eq) followed by methyl-4-oxo- 3-piperidine carboxylate.HCl (2.0 g, 10.4 mmol, 1 eq). The reaction mixture was heated to 70°C for 2 h, then cooled to r.t. The precipitate was filtered and washed with ethyl acetate (2 x 20 ml) to give a white solid which (2.2 g, 76percent) was not further purified
  • 3
  • [ 674793-32-9 ]
  • [ 171178-50-0 ]
  • [ 859173-98-1 ]
YieldReaction ConditionsOperation in experiment
~ 70% The acid was suspended in 40 mL DCM and brought to reflux. During reflux a clear solution was obtained. After 3 hours the reaction mixture was cooled to room temperature and the reaction mixture concentrated on a rotary evaporator. The residue was dried on a vacuum pump for 30 minutes. To this dry residue was added 30 mL acetonitrile, the amidine and DIPEA. The mixture was brought to reflux under nitrogen and maintained at reflux for 70 minutes. Analysis of the reaction mixture at this time (LCMS), showed one major peak, mass 294. The reaction mixture was cooled to room temperature and concentrated on a rotary evaporator to give a dry residue. 30 mL of methanol was added to this residue and a precipitate formed. The solid was filtered and washed with ether and dried under vacuum to give a solid, 0.8 g. This material was dissolved in DMF to obtain a clear solution and analyzed by LCMS. One major peak, mass 294. The filtrate was concentrated to a solid and then suspended in 50 mL water. A precipitate forms. This suspension was acidified to pH 1-2, with 10% HCl. The solid that separates was filtered and washed with ether and dried under high vacuum. The analysis of this product shows it to be identical to the solid obtained from the first crop. (2) 0.58 g of solid was obtained in this fashion. Both batches of solid were combined and used for further reactions. 1.38 g total yield. Approximate yield 70%.
 

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