Water → 3-{1-[6-(5-Bromopyrimidin-2-yl)pyridin-2-ylmethyl]-6-oxo-1,6-dihydropyridazin-3-yl}benzonitrile

HRID 1910855Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14]Br)[N:9]=2)=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[O:22]=[C:23]1[NH:28][N:27]=[C:26]([C:29]2[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=2)[C:32]#[N:33])[CH:25]=[CH:24]1.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[N:9]=[C:10]([CH2:14][N:28]3[C:23](=[O:22])[CH:24]=[CH:25][C:26]([C:29]4[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=4)[C:32]#[N:33])=[N:27]3)[CH:11]=[CH:12][CH:13]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2.3 54.6 mg (0.166 mmol) of 5-bromo-2-(6-bromomethylpyridin-2-yl)-pyrimidine and 54.1 mg (0.166 mmol) of caesium carbonate are added to a suspension of 32.7 mg (0.166 mmol) of 3-(6-oxo-1,6-dihydropyridazin-3-yl)benzonitrile in 0.5 ml of DMF, and the mixture is stirred for 18 hours at 80° C. The reaction mixture is added to water. The precipitate formed is filtered off with suction, washed with water and dried in vacuo, giving 3-{1-[6-(5-bromopyrimidin-2-yl)pyridin-2-ylmethyl]-6-oxo-1,6-dihydropyridazin-3-yl}benzonitrile as slightly brownish crystals; ESI 445, 447;

Workup

customThe precipitate formed
filtrationis filtered off with suction
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-67c8d1d186e04c7aadfc194d1522e68f
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604036B2

Reaction notes

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