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Chemical Structure| 89641-18-9 Chemical Structure| 89641-18-9
Chemical Structure| 89641-18-9

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Product Details of 2,4-Dimethoxypyrimidine-5-boronic acid

CAS No. :89641-18-9
Formula : C6H9BN2O4
M.W : 183.96
SMILES Code : COC1=NC(OC)=C(C=N1)B(O)O
MDL No. :MFCD01318985
InChI Key :LKGKUACPLXCVOF-UHFFFAOYSA-N
Pubchem ID :2736209

Safety of 2,4-Dimethoxypyrimidine-5-boronic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of 2,4-Dimethoxypyrimidine-5-boronic 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 [ 89641-18-9 ]

[ 89641-18-9 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 54044-79-0 ]
  • [ 89641-18-9 ]
  • [ 1138450-39-1 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 150℃; for 0.166667h;Microwave irradiation;Product distribution / selectivity; In a microwave vial, 2-bromo-5-methyl-1 ,3,4-thiadiazole (0.6 g, 3.26 mmol), [2,4- bis(methyloxy)-5-pyrimidinyl]boronic acid (0.780 g, 4.36 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.754 g, 0.652 mmol) in 1 ,2-Dimethoxyethane (DME) (12 ml) were stirred until dissolution of reactants, then sodium carbonate 1 M (9.78 ml, 9.78 mmol) was added and the mixture microwaved for 10 min at 15O0C. In another microwave vial, 2-bromo-5-methyl-1 ,3,4-thiadiazole (commercially available from Akos, 0.522 g, 2.84 mmol), [2,4-bis(methyloxy)-5-pyrimidinyl]boronic acid (0.780 g, 4.36 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.656 g, 0.568 mmol) in 1 ,2- Dimethoxyethane (DME) (12 ml) were stirred until dissolution of reactants, then sodium carbonate 1 M (8.51 ml, 8.51 mmol) was added and the mixture microwaved for 10 min at 15O0C. The two reaction mixtures were combined, water and AcOEt (50 +50 ml.) were added and organic layer separated. Combined organic layers were washed by water (3 x 50 ml_), dried upon sodium sulphate and concentrated under reduced pressure. Residue was purified by flash chromatography (Cy: EtOAc 1 :1 ) to give the title compound (637 mg, 2.272 mmol). 1H NMR (CHLOROFORM-d) delta ppm 9.30 (s, 1 H) 4.18 (s, 3 H) 4.1 1 (s, 3 H) 2.84 (s, 3 H)
  • 2
  • [ 120157-97-3 ]
  • [ 89641-18-9 ]
  • [ 1417540-94-3 ]
YieldReaction ConditionsOperation in experiment
91% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; at 90℃; for 18h;Inert atmosphere; Example 2 Synthesis of tert-butyl 4-(2,4-dimethoxypyrimidin-5-yl)phenethylcarbamate Industrial methylated spirits (IMS; 15 mL) and water (5 mL) were degassed thoroughly. tert-butyl 4-bromophenethylcarbamate (1.08 g, 3.63 mmol), sodium carbonate (1.54 g, 14.52 mmol), palladium tetrakis (0.42 g, 0.36 mmol) and 2,4-dimethoxy-5-pyrimidinylboronic acid (1.00 g, 5.44 mmol) were added and the reaction mixture heated to 90 C. for 18 hours. No starting material was observed by LCMS. Water (100 ml) and ethyl acetate (300 ml) were added and the organic layer separated. The organic layer was washed with water (100 ml), dried (MgSO4) and concentrated to give a yellow oil. The crude residue was subject to column chromatography (20 to 60% ethyl acetate/hexane) to give a yellow oil, tert-butyl 4-(2,4-dimethoxypyrimidin-5-yl)phenethylcarbamate, which crystallized on standing (1.18 g, 3.28 mmol, 91%).
  • 3
  • [ 1458-01-1 ]
  • [ 89641-18-9 ]
  • 3,5-diamino-N-carbamimidoyl-6-(2,4-dimethoxypyrimidin-5-yl)pyrazine-2-carboxamide [ No CAS ]
  • 4
  • [ 1458-01-1 ]
  • [ 89641-18-9 ]
  • methyl 3,5-diamino-6-(2,4-dimethoxypyrimidin-5-yl)pyrazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% 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.
 

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