Methyl 2-((dimethylamino)methyleneamino)-5,5-dimethylcyclohex-1-enecarboxylate → 6,6-Dimethyl-3,4,5,6,7,8-hexahydroquinazolin-4-one

HRID 240996Notes

Reaction equation

HRID 240996 reaction equation
C[N:2]([CH:4]=[N:5][C:6]1[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[CH2:8][C:7]=1[C:14]([O:16]C)=O)C>N.CO>[CH3:12][C:9]1([CH3:13])[CH2:10][CH2:11][C:6]2[N:5]=[CH:4][NH:2][C:14](=[O:16])[C:7]=2[CH2:8]1

Participants

4

Reactant 1

HCID 66820511Methyl 2-((dimethylamino)methyleneamino)-5,5-dimethylcyclohex-1-enecarboxylate

Product 1

HCID 1357423376,6-Dimethyl-3,4,5,6,7,8-hexahydroquinazolin-4-oneYield 90%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

A solution of methyl 2-((dimethylamino)methyleneamino)-5,5-dimethylcyclohex-1-enecarboxylate (9.5 g, 40 mol) in 7.0M ammonia in methanol (35 mL) was stirred at 25° C. for 90 minutes then concentrated to an oil. The residue was purified by silica gel column chromatography (ethyl acetate/hexanes, 1:8) to give 6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4(3H)-one (6.41 g, 90% yield) as a white solid. 1H NMR (400 MHz, d6-DMSO): 7.96 (s, 1H), 2.52 (t, 2H), 2.14 (s, 2H), 1.48 (t, 2H), 0.93 (s, 6H); MS (EI) for C10H14N2O: 179 (MH+).

Workup

  1. concentrationthen concentrated to an oil
  2. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexanes, 1:8)

Sources & evidence

ORD record
ord-c344a22a5c924a87ba7e81a3d94de53e
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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