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Chemical Structure| 1354455-93-8 Chemical Structure| 1354455-93-8

Structure of 1354455-93-8

Chemical Structure| 1354455-93-8

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Product Details of [ 1354455-93-8 ]

CAS No. :1354455-93-8
Formula : C11H12BrN3O
M.W : 282.14
SMILES Code : O=C1C2=NC=C(Br)C=C2NC(C(C)(C)C)=N1
MDL No. :MFCD28144718

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Application In Synthesis of [ 1354455-93-8 ]

* 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 [ 1354455-93-8 ]

[ 1354455-93-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1354455-93-8 ]
  • [ 380430-57-9 ]
  • [ 1354455-94-9 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In methanol; water; toluene; at 120℃; for 8h;Inert atmosphere; Microwave irradiation; Sealed tube; Example 5N-{4-[2-tert-Butyl-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrido[3,2-d]pyrimidin-7-yl]-phenyl}-methanesulfonamide (I-5); step 1-To a solution of 34a (1.05 g, 4.86 mmol, CASRN 669066-89-1), TEA (639 mg, 881 muL, 6.32 mmol) in DCM (15 mL) and THF (5 mL) was added dropwise pivaloyl chloride (586 mg, 598 muL, 4.86 mmol) and the resulting solution was stirred at RT. An another equivalent of TEA and 0.5 eq of pivaloyl chloride were added and the solution stirred over the weekend. The mixture was partitioned between DCM and H2O and neutralized with 1N HCl. The organic extract was washed with brine, dried (MgSO4), filtered and concentrated to afford 1.43 g (98%) of 34b which was used without additional purification.step 2-A solution of 34b (4.73 g, 15.8 mmol) and NaOH (3.15 mL, 31.5 mmol, 1 M EtOH solution) and EtOH (31.5 mL) was heated to reflux for 2.5 h which resulted in a homogenous solution. The reaction was cooled, diluted with EtOAc, washed sequentially with H2O and brine. The organic extract was dried (MgSO4), filtered and concentrated in vacuo. The resulting orange solid was triturated with Et2O to afford 2.63 g (59.2%) of 36a as a white solid which was used without additional purification.step 3-A microwave tube was charged with 36a (463 mg, 1.64 mmol), 4-(methylsulfonamido)phenyl boronic acid (370 mg, 1.72 mmol), and Na2CO3 (521 mg, 4.92 mmol), MeOH (3 mL), toluene (1.00 mL) and H2O (500 muL). The mixture was sparged with argon for 10 min and Pd(PPh3)4 (94.8 mg, 82.0 mumol) was added. Sparging with argon was continued for another 5 min. The vial was sealed and the reaction was heated thermally at 120 C. for 8 h. The mixture formed a yellow unstirrable opaque mixture. The mixture was diluted with H2O and stirred with aqueous acid which produced an insoluble white solid which was filtered and dried in vacuo to afford 0.606 g of 36b. The NMR was consistent with the desired product.step 4-To a suspension containing 36b (0.4 g, 1.07 mmol) DIPEA (236 mg, 316 IA, 1.83 mmol) in benzene (3 mL) was added POCl3 (98.8 mg, 60.1 muA, 644 mumol) and the mixture heated to reflux for 2 h. Additional POCl3 (20 uL) was added and refluxing continued for another 3 h. The reaction was sluggish. The reaction mixture was cooled to RT and concentrated in vacuo. The residue was diluted with EtOAc, stirred with ice and acidified to help solubilize the resultant brown solid. The mixture was extracted and the organic extracts washed sequentially with H2O satd. aq. NaHCO3H2O and brine. The resulting solution was dried (MgSO4), filtered and evaporated and dried under a high vacuum. The crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (35 to 60% EtOAc) to afford 0.151 g. of 36c.step 5-A microwave vial was charged with 36c (62.5 mg, 16 mumol), uracil (53.8 mg, 48 mumol) and Cs2CO3 (104 mg, 32 mumol) and DMSO (1.14 mL) to give a light brown suspension. The mixture was heated thermally in a sealed vial at 120 C. for 4. All SM was consumed. The crude product was purified on a preparative SiO2 TLC plate developed with 7% MeOH/DCM to afford 7.3 mg I-5.
 

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