ChemicalBook CAS DataBase List Pyrimidine-5-carboxaldehyde

Pyrimidine-5-carboxaldehyde synthesis

7synthesis methods

Product Name:Pyrimidine-5-carboxaldehyde
CAS Number:10070-92-5
Molecular formula:C5H4N2O
Molecular Weight:108.1

Under nitrogen, a solution of 5-bromopyrimidine (1 g, 6.3 mmol) in 60 mL anhydrous THF was added BuLi (2.5 M, 2.6 mL, 6.5 mmol) at -78° C. The resulting yellow solution was stirred for 20 min, after which ethyl formate (0.55 mL, 6.7 mmol) was added dropwise over 5 min. After 20 min, the reaction was quenched with 1.5 M THF/HCl solution (4.5 mL, 6.7 mmol). The cold bath was removed, and the reaction mixture was stirred for 1 h. THF was removed in vacco, 10 mL of water was then added. The mixture was extracted with CHCl3 (2*10 mL), and the combined organics were dried (MgSO4) and concentrated. The crude product was purified via flash column chromatography (5 per cent MeOH/CHCl3) to give 0.35 g (51 per cent) of the titled Pyrimidine-5-carboxaldehyde.

626-55-1 Synthesis

626-55-1
536 suppliers
$5.00/5 / G

4595-59-9 Synthesis

4595-59-9
459 suppliers
$6.00/1g

497-19-8
1378 suppliers
$13.00/300G

109-94-4 Synthesis

109-94-4
462 suppliers
$10.00/10g

10070-92-5
269 suppliers
$10.00/250mg

Yield:10070-92-5 35%

Reaction Conditions:

with hydrogenchloride;n-butyllithium in tetrahydrofuran;hexane;water

Steps:

15.1 1)
1) Preparation of pyrimidine-5-carbaldehyde A solution of 5-bromo-pyrimidine (5 g, 31.4 mmol, 1.0 eq.) in anhydrous THF (300 mL) was placed under an argon atmosphere in a three-necked round bottom flask equipped with a low-temperature thermometer. The mixture was cooled to -100°C in a EtOH/N₂(1) bath. To the solution of 5-bromopyridine was added a solution of n-BuLi in hexane (20 mL, 1.6 M, 32.5 mmol, 1.0 eq.). The resulting mixture was stirred for 20 minutes at 100°C and the organolithium that formed was trapped with a solution of ethyl formate (2.7 mL, 33.5 mmol, 1.1 eq.) in THF (10 mL). The reaction was stirred for another 20 minutes at 100°C and quenched with a solution of hydrochloric acid in ether (17 mL, 2M, 34 mmol). Then, the cold bath was removed and the mixture stirred at room temperature for 1 hour. The solution was concentrated under reduced pressure, and then treated with water and saturated aqueous sodium carbonate (10 mL). The mixture was extracted with dichloromethane and the organic layer was dried over MgSO₄. The solvent was removed under reduced pressure and the residue purified by silica gel flash-column chromatography (eluent: CH₂Cl₂/AcOEt, 60:40 to 50:50) to afford pyrimidine-5-carbaldehyde as beige crystals (1.2 g, 35%).

References:

Centre National de la Recherche Scientifique EP2266562, 2010, A1

4595-59-9 Synthesis

4595-59-9
459 suppliers
$6.00/1g

109-94-4 Synthesis

109-94-4
462 suppliers
$10.00/10g

10070-92-5
269 suppliers
$10.00/250mg

References

25193-95-7 Synthesis

25193-95-7
148 suppliers
$16.00/250mg

10070-92-5
269 suppliers
$10.00/250mg

References

109-94-4 Synthesis

109-94-4
462 suppliers
$10.00/10g

10070-92-5
269 suppliers
$10.00/250mg

References

4595-59-9 Synthesis

4595-59-9
459 suppliers
$6.00/1g

541-41-3
6 suppliers
$19.39/5g

10070-92-5
269 suppliers
$10.00/250mg

References

Pyrimidine-5-carboxaldehyde Related Search:

Silver sulfadiazine Uracil Pyrimidine Fluorocytosine Sulfadiazine Formaldehyde 5-METHYLCYTOSINE PYRIMIDINE-4-CARBOXALDEHYDE 2-Pyrimidinecarboxamide (6CI,7CI,9CI) PYRROLE-2-CARBONITRILE