1,1'-Carbonyldiimidazole → 3,4,4a,5-tetrahydro-5-methylpyrimido-[1,6-a]indol-1(2H)-one

HRID 1646753Notes

Reaction equation

HRID 1646753 reaction equation
[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]1[CH2:11][CH2:12][NH2:13].[C:14](N1C=CN=C1)(N1C=CN=C1)=[O:15]>O1CCCC1.C1(C)C=CC=CC=1>[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[C:14](=[O:15])[NH:13][CH2:12][CH2:11][CH:3]12

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 197871342-(2,3-Dihydro-3-methylindol-2-yl)ethylamine

Product 1

HCID 151870443,4,4a,5-tetrahydro-5-methylpyrimido-[1,6-a]indol-1(2H)-oneYield 47.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of crude 2-(2,3-dihydro-3-methylindol-2-yl)ethylamine (1.75 g) in tetrahydrofuran 12 ml) at room temperature was added in small portions 1,1'-carbonyldiimidazole (1.1 g). After being stirred for hours, the reaction mixture was evaporated in vacuo. The oil obtained was dissolved in toluene (25 ml) and the solution was heated at 110° C. for 1.5 hours. After evaporation of the solvent, the residue was purified by silica gel column chromatography (1% methanol-chloroform) to give crystals. Recrystallization from chloroform-ethyl acetate-hexane gave 3,4,4a,5-tetrahydro-5-methylpyrimido-[1,6-a]indol-1(2H)-one (0.65 g).

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. customThe oil obtained
  3. customAfter evaporation of the solvent
  4. customthe residue was purified by silica gel column chromatography (1% methanol-chloroform)
  5. customto give crystals
  6. customRecrystallization from chloroform-ethyl acetate-hexane

Sources & evidence

ORD record
ord-96437aa606294f14bf7cd1d97e375652
Source dataset
uspto-grants-1993_01
Patent number
US05180728

Reaction notes

Loading…