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Chemical Structure| 1272973-58-6 Chemical Structure| 1272973-58-6

Structure of 1272973-58-6

Chemical Structure| 1272973-58-6

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Product Details of [ 1272973-58-6 ]

CAS No. :1272973-58-6
Formula : C13H20N4O3
M.W : 280.32
SMILES Code : O=C(N1CCN(C2=NC=C(O)C=N2)CC1)OC(C)(C)C
MDL No. :MFCD23110950

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Application In Synthesis of [ 1272973-58-6 ]

* 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 [ 1272973-58-6 ]

[ 1272973-58-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1046816-75-4 ]
  • [ 1272973-58-6 ]
  • [ 1272974-11-4 ]
YieldReaction ConditionsOperation in experiment
43% Diisopropyl azodicarboxylate (0.140 mL, 0.71 mmol) was added to a stirred solution of tert-butyl 4-(5-hydroxypyrimidin-2-yl)piperazine-1-carboxylate (0.16 g, 0.57 mmol), and triphenylphosphine (0.225 g, 0.86 mmol) in THF (5 mL) under nitrogen. The resulting solution was stiffed at 20° C. for 30 minutes and then <strong>[1046816-75-4](2-chloropyrimidin-5-yl)methanol</strong> (0.083 g, 0.57 mmol) was added. The resulting solution was stirred at rt for 24 hours under nitrogen. The solvent was evaporated and the residue diluted with EtOAc and brine. A white ppt was filtered off and dried under vacuum. The aqueous layer was extracted with EtOAc (50 mL) and the combined organics were concentrated in vacuo to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 1 to 4percent MeOH in DCM. The crude product was purified by flash silica chromatography, elution gradient 40 to 100percent EtOAc in isohexane. Pure fractions were evaporated to dryness to afford tert-butyl 4-(5-((2-chloropyrimidin-5-yl)methoxy)pyrimidin-2-yl)piperazine-1-carboxylate (0.100 g, 43percent) as a white solid. 1H NMR (400.132 MHz, CDCl3) 1.49 (9H, s), 3.47-3.52 (4H, m), 3.71-3.75 (4H, m), 5.02 (2H, s), 8.14 (2H, s), 8.69 (2H, s). m/z (ES+) (M+H)+=407; HPLC tR=3.18 min.
  • 2
  • [ 940284-98-0 ]
  • [ 1272973-58-6 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide; In tetrahydrofuran; water; at 20℃; for 1.5h; In a vessel, tert-butyl 4-(5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyrimidin-2-yl)piperazine-l-carboxylate (0.5 g, 1.28 mmol) and 35% aqueous hydrogen peroxide (1.2 mL, 12.8 mmol) were dissolved in tetrahydrofuran (10 mL). The reaction mixture was stirred at room temperature for 1.5 hours. The mixture diluted to 40 mL with aqueous saturated sodium thiosulfate solution and then extracted with ethylacetate to give the desired product tert-butyl 4-(5-hydroxypyrimidin-2-yl)piperazine-l-carboxylate as a brown oil. This material was used in Step 2 without further purification.
 

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