N-methyl-2-pyrrolidone → HCID 178441845, compound

HRID 1975668Notes

Reaction equation

HRID 1975668 reaction equation
C[Si]([NH-])(C)C.C[Si]([NH-])(C)C.[Li+].[Li+].[Cl-].[Ce+3].[Cl-].[Cl-].[C:17]([C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25]([CH2:30][CH2:31][CH2:32][CH3:33])=[N:24][C:23]2=[O:34])(=[O:19])[CH3:18].[Cl-].[NH4+].[CH3:37][N:38]1[CH2:42][CH2:41][CH2:40][C:39]1=[O:43]>O1CCCC1>[CH2:30]([C:25]1[NH:26][C:27]2[C:22]([C:23](=[O:34])[N:24]=1)=[CH:21][C:20]([C:17]([OH:19])([CH:40]1[CH2:41][CH2:42][N:38]([CH3:37])[C:39]1=[O:43])[CH3:18])=[CH:29][CH:28]=2)[CH2:31][CH2:32][CH3:33]

Participants

7

Reactant 5

HCID 13387N-methyl-2-pyrrolidoneHCID 24636Cerium(III) chlorideHCID 25517Ammonium ChlorideHCID 86588160Lithim bis(trimethylsilylamide)HCID 178441846HCID 178441846, compound

Product 1

HCID 178441845HCID 178441845, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3.14 ml of 1-methyl-2-pyrrolidinone in 120 ml of dry tetrahydrofuran at -78° C. is added dropwise 32 8 ml of lithium bis(trimethylsilylamide)(1.0M in tetrahydrofuran followed by stirring for 1.5 hours. To the reaction mixture is added portionwise 8.07 g of cerium chloride and the mixture stirred for 1 hour at -70° C. To the mixture is added portionwise 2.0 g of 6-acetyl-2-butyl-4(1H)quinazolinone and the mixture stirred 5 hours at -70° C. The mixture is allowed to warm to 0° -hydroxy-1(1methyl-C. and stand overnight (0° C.). After addition of 60 ml of saturated ammonium chloride, the mixture is allowed to warm to room temperature and is filtered through diatomaceous earth which is washed with ethyl acetate. The filtrate is concentrated, the residue dissolved in ethyl acetate and the solution washed with 80 ml each of water, and brine and dried (Na2SO 4). The solvent is removed and the solid purified by high pressure liquid chromatography (HPLC) on silica with 2% methanol in ethyl acetate as solvent to give 2.21 g of product as a white glass. Anal. Calcd. for C19H25N3O3 1/2H2O:C,64.8;H,7.4; N,11.9. Found:C,64.1;H,7.6;N,11.9. Mass Spec MSFABL 344 (M+H).

Workup

  1. stirringthe mixture stirred for 1 hour at -70° C
  2. stirringthe mixture stirred 5 hours at -70° C
  3. temperatureto warm to 0° -hydroxy-1(1methyl-C
  4. waitand stand overnight
  5. custom(0° C.)
  6. filtrationis filtered through diatomaceous earth which
  7. washis washed with ethyl acetate
  8. concentrationThe filtrate is concentrated
  9. dissolutionthe residue dissolved in ethyl acetate
  10. washthe solution washed with 80 ml each of water, and brine
  11. dry with materialdried (Na2SO 4)
  12. customThe solvent is removed
  13. customthe solid purified by high pressure liquid chromatography (HPLC) on silica with 2% methanol in ethyl acetate as solvent

Sources & evidence

ORD record
ord-897c6cbfa9514c93b0dbeba66b8690eb
Source dataset
uspto-grants-1994_02
Patent number
US05288720

Reaction notes

Loading…