Potassium Carbonate → 3-Chloro-6-(oxetan-2-ylmethoxy)[1,2,4]triazolo[4,3-b]pyridazine

HRID 517809Notes

Reaction equation

[Cl:1][C:2]1[N:6]2[N:7]=[C:8](Cl)[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.[OH:12][CH2:13][CH:14]1[CH2:17][CH2:16][O:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([O:12][CH2:13][CH:14]3[CH2:17][CH2:16][O:15]3)[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

a mixture of 756 mg of commercial 3,6-dichloro[1,2,4]triazolo[4,3-b]pyridazine, 0.352 cm3 of 2-hydroxymethyloxetane and 552 mg of potassium carbonate in 8 cm3 of N,N-dimethylformamide is heated at 100° C. for 6 h and then stirred at 20° C. overnight. The reaction medium is concentrated to dryness under vacuum. The residue obtained is purified by chromatography on a Merck cartridge of 25 g of silica 15-40 μm by solid deposit, elution being carried out with a dichloromethane/methanol gradient of 100/0 to 97/03. 701 mg of 3-chloro-6-(oxetan-2-ylmethoxy)[1,2,4]triazolo[4,3-b]pyridazine are thus obtained in the form of a beige solid, the characteristics of which are as follows:

Workup

concentrationThe reaction medium is concentrated to dryness under vacuum
customThe residue obtained
customis purified by chromatography on a Merck cartridge of 25 g of silica 15-40 μm by solid deposit, elution

Sources & evidence

ORD record: ord-0cf7bdb542bd42b9958625e0d297b56a
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115134B2

Reaction notes

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