N-methyl-2-pyrrolidone → HCID 178441856, compound

HRID 1975667Notes

Reaction equation

[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C:3]1=[O:7].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:18]([C:22]1[NH:23][C:24]2[C:29]([C:30](=[O:32])[N:31]=1)=[CH:28][C:27]([CH:33]=[O:34])=[CH:26][CH:25]=2)[CH2:19][CH2:20][CH3:21]>O1CCCC1>[CH2:18]([C:22]1[NH:23][C:24]2[C:29]([C:30](=[O:32])[N:31]=1)=[CH:28][C:27]([CH:33]([OH:34])[CH:4]1[CH2:5][CH2:6][N:2]([CH3:1])[C:3]1=[O:7])=[CH:26][CH:25]=2)[CH2:19][CH2:20][CH3:21]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 0.834 ml of 1-methyl-2-pyrrolidinone in 10 ml of tetrahydrofuran is added dropwise with stirring 8.69 ml of lithium bis(trimethylsilyl)amide (1.0M in tetrahydrofuran) at -78° C. Following complete addition, 500 mg of 2-butyl-1,4-dihydro-4-oxo-6-quinazolinecarboxaldehyde is rapidly added and the reactants stirred at -78° C. for 4 1/2 hours. The reaction mixture is quenched with 10 ml of saturated ammonium chloride and allowed to warm to room temperature followed by evaporation of the volatiles in vacuo to a residue. The residue is diluted with 5 ml of water and extracted with ethyl acetate. The extract is washed with water, brine and dried with anhydrous Na2SO4.

Workup

additionis rapidly added
customThe reaction mixture is quenched with 10 ml of saturated ammonium chloride
temperatureto warm to room temperature
customfollowed by evaporation of the volatiles in vacuo to a residue
additionThe residue is diluted with 5 ml of water
extractionextracted with ethyl acetate
washThe extract is washed with water, brine
dry with materialdried with anhydrous Na2SO4

Sources & evidence

ORD record: ord-0367f48a9e3c443b9f50cda15e7cec58
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05288720

Reaction notes

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