9-tert-Butyl-2,4-di(pyrrolidin-1-yl)-9H-pyrimido[4,5-b]indole → HCID 15521617, compound

HRID 482325Notes

Reaction equation

HRID 482325 reaction equation
C([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]2[C:14]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[N:15][C:16]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[N:17][C:6]1=2)(C)(C)C>FC(F)(F)C(O)=O>[N:18]1([C:16]2[N:15]=[C:14]([N:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[C:7]3[C:8]4[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=4)[NH:5][C:6]=3[N:17]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

3

Reactant 1

HCID 543682569-tert-Butyl-2,4-di(pyrrolidin-1-yl)-9H-pyrimido[4,5-b]indole

Product 1

HCID 15521617HCID 15521617, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 9-t-butyl-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole (XII, EXAMPLE 25, 4.0 g) and 100 mL of trifluoroacetic acid is heated at reflux for 2 hr. Approximately one-half of the trifluoroacetic acid is removed by distillation. The reaction mixture is then cooled to 0°, made basic with 25% aqueous sodium hydroxide and extracted with methylene chloride. The combined organic phases are washed with saline, dried over anhydrous sodium sulfate and concentrated. Chromatography (silica gel, 5% ethyl acetate/methylene chloride) gives the title compound, NMR (CDCl3) 7.89, 7.86, 7.26-7.09, 3.95, 3.67 and 2.01-1.95 δ.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 hr
  3. customApproximately one-half of the trifluoroacetic acid is removed by distillation
  4. temperatureThe reaction mixture is then cooled to 0°
  5. extractionextracted with methylene chloride
  6. washThe combined organic phases are washed with saline
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2011a2f170b84ce59a1c20d5cd4dac11
Source dataset
uspto-grants-1998_08
Patent number
US05795986

Reaction notes

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