2-Chloropyrimidine → HCID 19040774, compound

HRID 1683911Notes

Reaction equation

HRID 1683911 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14].Cl[C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH3:15][N:13]([CH3:14])[CH2:12][CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:17]3[N:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:3]=2)[NH:7][CH:6]=1

Participants

5

Reactant 3

HCID 744042-ChloropyrimidineHCID 517045Sodium AcetateHCID 118202113-(2-DIMETHYLAMINO-ETHYL)-1H-INDOL-5-YLAMINE

Product 1

HCID 19040774HCID 19040774, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Amino-3-(2-dimethylaminoethyl)-1H-indole and 2-chloropyrimidine were used, Sodium acetate was used as base, acetic acid was used as solvent, and the reaction was heated at reflux for 12 hours. Column chromatography afforded the title compound (11%) as a yellow solid: 13C NMR (CD3OD) δ162.6, 159.2, 135.4, 132.2, 128.9, 124.0, 118.6, 113.7, 112.6, 112.4, 112.3, 61.3, 45.4, 24.3; HRMS calculated for C16H19N5 281.1642, found 281.1660. Anal. calcd for C16H19N5.0.5C2H4O2 [acetic acid]: C, 65.62; H, 6.80; N, 22.51. Found: C, 65.74; H, 6.68; N, 22.60.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 12 hours

Sources & evidence

ORD record
ord-e765168daf994707b1971e3c7e1f2a93
Source dataset
uspto-grants-1997_06
Patent number
US05639752

Reaction notes

Loading…