Imidazole → 9-[2-(1-Imidazolyl)ethyl]-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole

HRID 482322Notes

Reaction equation

HRID 482322 reaction equation
CS(O[CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[C:17]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[N:18][C:19]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:20][C:9]1=2)(=O)=O.[NH:31]1[CH:35]=[CH:34][N:33]=[CH:32]1>C1(C)C(C)=CC=CC=1>[N:31]1([CH2:6][CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3[C:17]([N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[N:18][C:19]([N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[N:20][C:9]2=3)[CH:35]=[CH:34][N:33]=[CH:32]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 537324089-(2-Methanesulfonyloxyethyl)-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole

Product 1

HCID 190640889-[2-(1-Imidazolyl)ethyl]-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 9-(2-methanesulfonyloxyethyl)-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole (IX, EXAMPLE4, 0.64 g), imidazole (1.02 g) and xylene (15 mL) is heated at reflux for 3 hr. The xylene is then removed under reduced pressure, and the residue is partitioned between methylene chloride and aqueous sodium bicarbonate. The organic phase is washed with saline, dried over sodium sulfate and concentrated. Chromatography (silica gel, 4% methanol/methylene chloride) gives the title compound, mp=181°-183°; NMR (CDCl3) 7.88, 7.40, 7.14-7.09, 7.01-6.97, 6.82, 4.56-4.54, 4.44-4.42, 3.92, 3.63 and 1.99 δ.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 hr
  3. customThe xylene is then removed under reduced pressure
  4. customthe residue is partitioned between methylene chloride and aqueous sodium bicarbonate
  5. washThe organic phase is washed with saline
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-86a5c43cf7724ebf9cfa85c4e4cc492c
Source dataset
uspto-grants-1998_08
Patent number
US05795986

Reaction notes

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