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

HRID 1489609Notes

Reaction equation

HRID 1489609 reaction equation
N1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2C=NC=1)=CC=CC=3.Cl.[Cl:15][C:16]1[C:17]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][C:18]=2[N:19]=[CH:20][N:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:35][C:36](C)=O>C(Cl)Cl>[Cl:15][C:16]1[C:17]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH2:35][CH2:36][N:7]([CH2:6][CH3:5])[CH2:8][CH3:13])[C:18]=2[N:19]=[CH:20][N:21]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 10796Cesium carbonateHCID 125093309H-Pyrimido(4,5-b)indoleHCID 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

4-Chloro-9N-(2-N,N-dimethylamino)ethyl)indolo[2,3-d]pyrimidine. 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-39b2b2215fec4963bd104b605dc8a2ec
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

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