Acetone → 4-chloro-9N-(2-(N,N-diethylamino)ethyl)indolo[2,3-d]pyrimidine

HRID 1358290Notes

Reaction equation

HRID 1358290 reaction equation
Cl.[Cl:2][C:3]1[C:4]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:5]=2[N:6]=[CH:7][N:8]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C[C:23]([CH3:25])=O>C(Cl)Cl>[Cl:2][C:3]1[C:4]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([CH2:4][CH2:5][N:9]([CH2:23][CH3:25])[CH2:10][CH3:11])[C:5]=2[N:6]=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 10796Cesium carbonateHCID 181843914-Chloroindolo[2,3-d]pyrimidine hydrochloride

Product 1

HCID 108282474-chloro-9N-(2-(N,N-diethylamino)ethyl)indolo[2,3-d]pyrimidineYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-chloroindolo[2,3-d]pyrimidine hydrochloride (407 mg, 2 mmol), 2-N,N-diethylaminoethyl chloride hydrochloride (413 mg, 2.4 mmol), anhydrous cesium carbonate (1.95 g, 6 mmol) and 4 molecular sieves (1.5 g) in acetone (6 mL) are heated at reflux under a nitrogen atmosphere for 1.5 h. The mixture is filtered through celite, washing the filter cake with acetone (4×10 ml), followed by concentration of the filtrate under reduced pressure affording a viscous amber oil, which is dissolved in CH2Cl2, (20 ml), and washed with water (2×25 mL), dried (MgSO4), and the solvent is removed in vacuo. The crude product is chromatographed on silica, eluting with 4% methanol/chloroform to give 4-chloro-9N-(2-(N,N-diethylamino)ethyl)indolo[2,3-d]pyrimidine (495 mg, 82%), as a pale yellow oil. 1H NMR (DMSO) δ8.79 (1H, s), 8.41 (1H, d, J=8.0 Hz), 7.66-7.58 (2H, m), 7.46-7.42 (1H, m), 4.57 (2H, t, J=6.8 Hz), 2.90 (2H, t, J=7.1 Hz), 2.63 (4H, d, J=7.0 Hz), 0.99 (6H, t, J=7.0 Hz).

Workup

  1. temperatureare heated
  2. temperatureat reflux under a nitrogen atmosphere for 1.5 h
  3. filtrationThe mixture is filtered through celite
  4. washwashing the filter cake with acetone (4×10 ml)
  5. customaffording a viscous amber oil, which
  6. washwashed with water (2×25 mL)
  7. dry with materialdried (MgSO4)
  8. customthe solvent is removed in vacuo
  9. customThe crude product is chromatographed on silica
  10. washeluting with 4% methanol/chloroform

Sources & evidence

ORD record
ord-1c32b353aa6b49e19afb7f639bbace08
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

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