Cesium carbonate → 2-Bromo-3-(but-2-ynyl)-5-(4-methyl-quinazolin-2-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one

HRID 2214456Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[Br:7][C:8]1[N:9]([CH2:18][C:19]#[C:20][CH3:21])[C:10]2[C:15](=[O:16])[NH:14][N:13]=[CH:12][C:11]=2[N:17]=1.Cl[CH2:23][C:24]1[N:33]=[C:32]([CH3:34])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=1>CN(C)C=O.O>[Br:7][C:8]1[N:9]([CH2:18][C:19]#[C:20][CH3:21])[C:10]2[C:15](=[O:16])[N:14]([CH2:23][C:24]3[N:33]=[C:32]([CH3:34])[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)[N:13]=[CH:12][C:11]=2[N:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

489 mg (1.5 mmol) of caesium carbonate were added to a solution of 300 mg (1.12 mmol) of 2-bromo-3-(but-2-ynyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one and 260.1 mg (1.35 mmol) of 2-chloromethyl-4-methyl-quinazoline in 4.0 ml of dimethylformamide and this mixture was stirred for 2 hours under an argon atmosphere at 80° C. Then it was diluted with 10 ml of water and stirred for 30 minutes at ambient temperature. The crude product precipitated was suction filtered and purified by column chromatography (silica gel; eluant:petroleum ether with 20–50% ethyl acetate).

Workup

stirringstirred for 30 minutes at ambient temperature
customThe crude product precipitated
filtrationfiltered
custompurified by column chromatography (silica gel; eluant:petroleum ether with 20–50% ethyl acetate)

Sources & evidence

ORD record: ord-0076b42d6ff141e5a639ced9c6c6aaab
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109192B2

Reaction notes

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