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Chemical Structure| 109299-78-7 Chemical Structure| 109299-78-7
Chemical Structure| 109299-78-7

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Product Details of 5-Pyrimidylboronic acid

CAS No. :109299-78-7
Formula : C4H5BN2O2
M.W : 123.91
SMILES Code : C1=NC=C(B(O)O)C=N1
MDL No. :MFCD03002366
InChI Key :HZFPPBMKGYINDF-UHFFFAOYSA-N
Pubchem ID :2795193

Safety of 5-Pyrimidylboronic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 5-Pyrimidylboronic acid

* 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 [ 109299-78-7 ]

[ 109299-78-7 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 13195-50-1 ]
  • [ 109299-78-7 ]
  • [ 58759-03-8 ]
  • 2
  • [ 669066-35-7 ]
  • [ 109299-78-7 ]
  • [ 1428882-00-1 ]
YieldReaction ConditionsOperation in experiment
68.2% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 85℃; for 17h;Inert atmosphere; Preparation 92A: 3-Fluoro-4-(p rimidin-5-yl)picolinonitrile[00317] A vial containing a mixture of <strong>[669066-35-7]3-fluoro-4-iodopicolinonitrile</strong> (1.25 g, 5.04 mmol), pyrimidin-5-ylboronic acid (1.249 g, 10.08 mmol), and cesium carbonate (3.45 g, 10.58 mmol) in dioxane (Ratio: 2.0, Volume: 10.18 ml) and water (Ratio: 1.000, Volume: 5.09 ml) was degassed with N2 for 5 min, then PdCl2(dppf)-CH2Cl2Adduct (0.218 g, 0.267 mmol) was added. The solution was heated at 85 C for 17 hr, and then allowed to cool to room temperature. The reaction was quenched with water. The reaction mixture was diluted with EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc (3X). The organic phases were combined, dried over Na2S04, filtered, and concentrated to afford a brown residue. The crude material was purified by MPLC (80 g column, 60 mL/min, 30-100% EtOAc in hexanes) to give the title compound (695 mg, 3.44 mmol, 68.2% yield) as a pink solid. ESI MS (M+H)+ = 201.1.
  • 3
  • [ 21193-80-6 ]
  • [ 109299-78-7 ]
  • 4-amino-5-(pyrimidin-5-yl)-N7-(β-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; water; at 20 - 100℃; for 38.0h;Inert atmosphere; (0.17 g, 0.50 mmol, 1 eq.), pyrimidin-5-yl-boronic acid (0.092 g, 0.75 mmol, 1.5 eq.), Pd2(dba)3 (0.005 g,0.005 mmol, 0.01 eq.) and P(c-hexyl)3 (0.0035 g, 0.012 mmol, 0.024eq.) were added to a 10mL round-bottom flask containing a stir bar.Next, the flask was evacuated and refilled with argon three times.Then, 1,4-dioxane was added (1.33 mL, 2.67 mL/mmol SM) togetherwith 1.27M aq. K3PO4 solution (0.67 mL, 1.3 mL/mmol). The flaskwas stirred at ambient temperature for ~5 min and then transferred to a pre-heated oil bath at 100 C. Heating was continued for 38 h,after which the mixture was cooled to ambient temperature. Themixture was neutralized (pH ~ 7) with 0.5M aq. HCl. The mixturewas evaporated till dryness re-suspended in MeOH and evaporated(three times). Next, the mixture was adsorbed onto Celite (fromMeOH) and eluted over a short silica pad (~5 cm) with 20% MeOH/DCM. The liquid was evaporated in vacuo and purified by columnchromatography 5/20% MeOH/EA. 18 was isolated as a yellowsolid (0.045 g, 0.13 mmol). Yield 26%. Melting point: 275 C(decomposed). 1H NMR (300 MHz, DMSO-d6) delta: 3.50-3.57 (m, 1H,H-5??), 3.60-3.67 (m, 1H, H-5'), 3.91 (q, J 3.6 Hz, 1H, H-4'),4.09-4.14 (m, 1H, H-3'), 4.45 (dd, J 11.1, 5.7 Hz, 1H, H-2'),5.14-5.18 (m, 2H, OH-3' , OH-5'), 5.36 (d, J 6.0 Hz, 1H, OH-2'), 6.13(d, J 6.0 Hz, 1H, H-1'), 6.51 (br. s, 2H, NH2), 7.77 (s, 1H, H-6), 8.18 (s,1H, H-2), 8.86 (s, 2H, H-4Pyrim, H-6Pyrim), 9.13 (s, 1H, H-2Pyrim). 13CNMR (75 MHz, DMSO-d6) delta: 61.6 (C-5'), 70.5 (C-3'), 73.8 (C-2'), 85.2(C-4'), 87.1 (C-1?), 100.3 (C-4a), 109.3 (C-5), 122.8 (C-6), 128.5 (C-5Pyrim), 151.4 (C-7a), 152.0 (C-2), 155.5 (2C, C-4Pyrim, C-6Pyrim), 156.2(C-2Pyrim), 157.6 (C-4). HRMS (ESI): calculated for C15H17N6O4([MH]): 345.1306, found: 345.1329.
  • 4
  • [ 1458-01-1 ]
  • [ 109299-78-7 ]
  • methyl 3,5-diamino-6-(pyrimidin-5-yl)pyrazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In methanol; toluene;Inert atmosphere; Reflux; General procedure: <strong>[1458-01-1]Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate</strong> 2 (1 eq.) was combined with K2CO3 (10 eq.), the appropriate (het)aryl boronic acid (1.5 eq.) and Pd(PPh3)4 (5 mol%) in a two-neck round bottom flask. The flask was connected to a condenser and purged with nitrogen. A 4:1 mixture of anhydrous toluene: MeOH (60 mL) was added via syringe and the reaction mixture was heated at reflux for 0.5-18 h. The mixture was allowed to cool to room temperature and filtered through Celite (10 x 3 cm, eluting with 3 x 20 mL EtOAc). The filtrate was evaporated to dryness and the residue purified by silica gel flash column chromatography using EtOAc/pet spirit.
  • 5
  • [ 955368-90-8 ]
  • [ 109299-78-7 ]
  • C13H12N6OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; oxygen; In dichloromethane; at 20 - 25℃; for 32h; Copper acetate (81.72 mg, 449.90 mumol) and pyridine (284.70 mg, 3.60 mmol, 290.51 muL) were added into I1 (100.00 mg, 449.90 mumol) and 5-pyrimidinylboronic acid (111.49 mg, 899.80 mumol) in dichloromethane (10.00 mL) solution. Under oxygen atmosphere, the mixture was stirred at 20-25C for 32 hours, EtOAc (180 mL), washed by water 240 mL (120 mL ×2) and saturated brine 120 mL, dried over anhydrous sodium sulfate, then filtered and concentrated to give the crude compound 6-A, which was purified by thin phase chromatography (PE/EtOAc =2/1) to give compound 6-A. MS m/z: 300.9[M+H]+
 

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