Benzaldehyde → 1-Ethyl-6-methyl-3-phenyl-1H-pyrimido[5,4-e][1,2,4]triazine-5,7-dione

HRID 16144Notes

Reaction equation

[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([N:11]([C:13]1[NH:18][C:17](=[O:19])[N:16]([CH3:20])[C:15](=[O:21])[CH:14]=1)[NH2:12])[CH3:10].[N:22]([O-])=O.[Na+]>C(O)(=O)C>[CH2:9]([N:11]1[C:13]2=[N:18][C:17](=[O:19])[N:16]([CH3:20])[C:15](=[O:21])[C:14]2=[N:22][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:12]1)[CH3:10]

Participants

Conditions

Temperature: 10 °C

Procedure

Benzaldehyde (55 μl, 0.54 mmol) is added to a solution of compound 3 (115 mg, 0.54 mmol) in glacial acetic acid (2 ml) and the mixture is stirred at 10° C. for 20 min. An aqueous solution of sodium nitrite (40 mg of NaNO2 in 100 μl of water) is then added and the mixture is stirred at 10° C. for a further 30 min. The mixture is poured onto ice water and the product is extracted with ethyl acetate (3×30 ml). The organic phases are dried (Na2SO4) and the solvent is distilled off in vacuo. The residue is purified by flash chromatography (7:3, toluene/ethyl acetate). 1-Ethyl-6-methyl-3-phenyl-1H-pyrimido[5,4-e][1,2,4]triazine-5,7-dione (44 mg, 28.8%) and 1-ethyl-4-oxy-3-phenyl-6-propyl-1H-pyrimido[5,4-e][1,2,4]triazine-5,7-dione (41 mg, 32%) are obtained.

Workup

stirringthe mixture is stirred at 10° C. for a further 30 min
additionThe mixture is poured onto ice water
extractionthe product is extracted with ethyl acetate (3×30 ml)
dry with materialThe organic phases are dried (Na2SO4)
distillationthe solvent is distilled off in vacuo
customThe residue is purified by flash chromatography (7:3, toluene/ethyl acetate)

Sources & evidence

ORD record: ord-c3686d7e7e4c4fd4b7873adb9e8b4cb9
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737144B2

Reaction notes

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