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Chemical Structure| 1260585-11-2 Chemical Structure| 1260585-11-2

Structure of 1260585-11-2

Chemical Structure| 1260585-11-2

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Product Details of [ 1260585-11-2 ]

CAS No. :1260585-11-2
Formula : C8H7ClF3N3O
M.W : 253.61
SMILES Code : O=C1C=C(Cl)N=C2N[C@H](C(F)(F)F)CCN21
MDL No. :MFCD29477478

Safety of [ 1260585-11-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 1260585-11-2 ]

* 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 [ 1260585-11-2 ]

[ 1260585-11-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1260585-11-2 ]
  • [ 31560-06-2 ]
  • (2S)-8-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-2-(trifluoromethyl)-1,2,3,4-tetrahydropyrimido[1,2-a]pyrimidin-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.2 g With triethylamine; at 130℃; for 6h;Sealed tube; 1.60 g (6.31 mmol) of (8S)-2-chloro-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 1.30 g (9.46 mmol) of <strong>[31560-06-2](1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride</strong> are mixed together. The powder obtained is placed in a tube and 2.21 mL (15.77 mmol) of triethylamine are added. The tube is sealed and heated at 130°C in an oil bath for 6 hours. After cooling, the crude product is purified by chromatography on silica gel (eluent: 95/5 EtOAc/MeOH). After evaporating the fractions under reduced pressure, 1.20 g of (8S)-2-(1S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-yl-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one are obtained, the characteristics of which are as follows: LC/MS (method G): ESI+: [M+H]+: m/z 317 tr (min) = 1.37. 1H NMR (300 MHz, delta in ppm, CDCl3): 2 (m, 2H), 2.35 (m, 2H), 3.45 (m, 2H), 3.92 (s, 1 H), 3.95-4.32 (m, 4H), 4.78 (s, 1 H), 4.89-5.2 (bs, 1 H), 5.49-5.77 (bs, 1 H).
1.20 g With triethylamine; at 130℃; for 6h;Sealed tube; 1.60 g (6.31 mmol) of (8S)-2-chloro-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 1.30 g (9.46 mmol) of <strong>[31560-06-2](1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride</strong> are mixed together. The powder obtained is placed in a tube and 2.21 mL (15.77 mmol) of triethylamine are added. The tube is sealed and heated at 130° C. in an oil bath for 6 hours. After cooling, the crude product is purified by chromatography on silica gel (eluent: 95/5 EtOAc/MeOH). After evaporating the fractions under reduced pressure, 1.20 g of (8S)-2-(1S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-yl-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one are obtained, the characteristics of which are as follows: LC/MS (method G): ESI+: [M+H]+: m/z 317 tr (min)=1.37 1H NMR (300 MHz, delta in ppm, CDCl3): 2 (m, 2H), 2.35 (m, 2H), 3.45 (m, 2H), 3.92 (s, 1H), 3.95-4.32 (m, 4H), 4.78 (s, 1H), 4.89-5.2 (bs, 1H), 5.49-5.77 (bs, 1H).
  • 2
  • [ 141095-78-5 ]
  • [ 1260585-11-2 ]
  • (8S)-2-chloro-9-[2-oxo-2-(tetrahydropyran-4-yl)ethyl]-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
220 mg A suspension of 150 mg (0.591 mmol) of (8S)-2-chloro-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 578.13 mg (1.77 mmol) of cesium carbonate in 10 mL of acetonitrile is stirred for 15 minutes at room temperature. 146.97 mg (0.709 mmol) of <strong>[141095-78-5]2-bromo-1-(tetrahydropyran-4-yl)ethanone</strong> are then added. After stirring overnight at room temperature, the reaction mixture is evaporated and the residue is taken up in water and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness to give 220 mg of (8S)-2-chloro-9-[2-oxo-2-(tetrahydropyran-4-yl)ethyl]-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one, corresponding to the following characteristics: LC/MS (method G): ESI+ [M+H]+: m/z 380. tr (min) = 1 .94. 1H NMR (300 MHz, delta in ppm, CDCl3): 1.58-2.04 (m, 2H), 2.37 (m, 1 H), 2.5 (m, 1 H), 2.76 (m, 1 H), 3.5 (4H), 3.9 (d, 1 H), 3.96-4.02 (m, 4H), 4.6 (m, 1 H), 5.25 (d, 1 H), 5.99 (s, 1 H).
220 mg A suspension of 150 mg (0.591 mmol) of (8S)-2-chloro-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 578.13 mg (1.77 mmol) of cesium carbonate in 10 mL of acetonitrile is stirred for 15 minutes at room temperature. 146.97 mg (0.709 mmol) of <strong>[141095-78-5]2-bromo-1-(tetrahydropyran-4-yl)ethanone</strong> are then added. After stirring overnight at room temperature, the reaction mixture is evaporated and the residue is taken up in water and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness to give 220 mg of (8S)-2-chloro-9-[2-oxo-2-(tetrahydropyran-4-yl)ethyl]-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one, corresponding to the following characteristics: LC/MS (method G): ESI+ [M+H]+: m/z 380 tr (min)=1.94 1H NMR (300 MHz, delta in ppm, CDCl3): 1.58-2.04 (m, 2H), 2.37 (m, 1H), 2.5 (m, 1H), 2.76 (m, 1H), 3.5 (4H), 3.9 (d, 1H), 3.96-4.02 (m, 4H), 4.6 (m, 1H), 5.25 (d, 1H), 5.99 (s, 1H).
  • 3
  • [ 280-13-7 ]
  • [ 1260585-11-2 ]
  • (2S)-8-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-(trifluoromethyl)-1,2,3,4-tetrahydropyrimido[1,2-a]pyrimidin-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
600 mg With triethylamine; at 150℃; for 0.166667h;Microwave irradiation; 500 mg (1.97 mmol) of (8S)-2-chloro-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one, 884 mg (5.91 mmol) of 8-oxa-3-azabicyclo[3.2.1]octane and 820 μl (5.91 mmol) of triethylamine are placed in a microwave tube. The mixture is irradiated for 10 minutes at 150 C. The reaction medium is purified directly by passing through an RP18 reverse-phase column (eluent: H2O: 100% to CH3CN: 100%) to give 600 mg of (8S)-2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one, the characteristics of which are as follows: LC/MS (method A): ESI+ [M+H]+: m/z 331 tr (min)=0.53 1H NMR (600 MHz, δ in ppm, DMSO-d6): 1.66 (m, 2H), 1.81 (m, 2H), 2.09 (m, 1H), 2.2 (m, 1H), 2.89 (d, 2H), 3.34 (m, 1H), 3.75 (m, 2H), 4.14 (m, 1H), 4.26 (s, 1H), 4.37 (s, 2H), 4.84 (s, 1H), 8.17 (s, 1H).
 

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