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

HRID 1453542Notes

Reaction equation

HRID 1453542 reaction equation
[Br:1][C:2]1[N:3]([CH2:12][C:13]#[C:14][CH3:15])[C:4]2[C:9](=[O:10])[NH:8][N:7]=[CH:6][C:5]=2[N:11]=1.Cl[CH2:17][C:18]1[N:27]=[C:26]([CH3:28])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[N:3]([CH2:12][C:13]#[C:14][CH3:15])[C:4]2[C:9](=[O:10])[N:8]([CH2:17][C:18]3[N:27]=[C:26]([CH3:28])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)[N:7]=[CH:6][C:5]=2[N:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2415182-(Chloromethyl)-4-methylquinazolineHCID 219476582-Bromo-3-(but-2-ynyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one

Product 1

HCID 160377782-Bromo-3-(but-2-ynyl)-5-(4-methyl-quinazolin-2-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 365 mg 2-bromo-3-(2-butyn-1-yl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one, 265 mg 2-chloromethyl-4-methyl-quinazoline and 210 mg potassium carbonate in 6 ml acetonitrile is stirred for 17 h at ambient temperature. Then the reaction mixture is filtered through 5 g aluminium oxide with ethyl acetate and the filtrate is evaporated down. The residue is triturated in diisopropylether, separated from the ether and dried.

Workup

  1. filtrationThen the reaction mixture is filtered through 5 g aluminium oxide with ethyl acetate
  2. customthe filtrate is evaporated down
  3. customThe residue is triturated in diisopropylether
  4. customseparated from the ether
  5. customdried

Sources & evidence

ORD record
ord-5e1303b1d90540ba8b0d67eb9bde0c84
Source dataset
uspto-grants-2009_01
Patent number
US07476671B2

Reaction notes

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