ChemicalBook CAS DataBase List Pyridazin-3-ylmethanol

Pyridazin-3-ylmethanol synthesis

6synthesis methods

Product Name:Pyridazin-3-ylmethanol
CAS Number:37444-46-5
Molecular formula:C5H6N2O
Molecular Weight:110.11

To a solution of ethyl pyridazine-3-carboxylate (0.641 g, 4.21 mmol) in THF (20 mL) at 0 °C has added a solution of lithium aluminium hydride in tetrahydrofuran (1.0 M, 4.21 mL, 4.21 mmol) dropwise. The resulting suspension was stirred for 30 min. Solid Na2S04 *10 H20 was added, and the mixture was diluted with EtOAc and stirred for lh. The mixture was filtered through a pad of celite, and the residual solid was washed with EtOAc several times. The filtrate was concentrated under reduced pressure. The crude product was purified by silica gel chromatography to afford the product Pyridazin-3-ylmethanol as a brown solid (120 mg 26 percent).

Pyridazine-3-carboxylic acid ethyl ester

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Yield: 26%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 0; for 0.5 h;

Steps:

71.2 Step 2: pyridazin-3-ylmethanol
To a solution of ethyl pyridazine-3-carboxylate (0.641 g, 4.21 mmol) in THF (20 mL) at 0 °C was added a solution of lithium aluminum hydride in tetrahydrofuran (1.0 M, 4.21 mL, 4.21 mmol) dropwise. The resulting suspension was stirred for 30 min. Solid Na₂S0₄ *10 H₂0 was added and the mixture was diluted with EtOAc and stirred for lh. The mixture was filtered through a pad of celite and the residual solid was washed with EtOAc several times. The filtrate was concentrated under reduced pressure. The crude product was purified by silica gel chromatography to afford the product as brown solid (120 mg, 26%). LCMS (AA): m/z 111 (M+H).

References:

MILLENNIUM PHARMACEUTICALS, INC.;ADHIKARI, Sharmila;CALDERWOOD, Emily, Frances;ENGLAND, Dylan, Bradley;GOULD, Alexandra, E.;HARRISON, Sean, J.;HUANG, Shih-Chung;MA, Liting WO2018/89786, 2018, A1 Location in patent:Paragraph 00398