Sodium hydride → HCID 66875264, compound

HRID 2381374Notes

Reaction equation

HRID 2381374 reaction equation
[CH:1]1([OH:5])[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[Cl:8][C:9]1[C:10](=[O:22])[N:11]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[N:12]=[CH:13][C:14]=1Cl>O1CCCC1>[Cl:8][C:9]1[C:10](=[O:22])[N:11]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[N:12]=[CH:13][C:14]=1[O:5][CH:1]1[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76218CyclobutanolHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×

Product 1

HCID 66875264HCID 66875264, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of cyclobutanol (7.2 g, 100 mmol) in tetrahydrofuran (200 mL) was treated with sodium hydride (3.6 g, 150 mmol) and stirred at 25° C. for 15 min. At this time, 4,5-dichloro-2-(tetrahydropyran-2-yl)-2H-pyridazin-3-one (Intermediate 20, 20.0 g, 80 mmol) in tetrahydrofuran was added dropwise. The resulting mixture was stirred at 25° C. for 2 h. At this time, the reaction was concentrated in vacuo. Chromatography (8/1 petroleum ether/ethyl acetate) afforded 4-chloro-5-cyclobutoxy-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one (16.3 g, 72%).

Workup

  1. stirringThe resulting mixture was stirred at 25° C. for 2 h
  2. concentrationAt this time, the reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-4596137be41a4188a058123b7d3dc279
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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