Water → 5-(2,6-Diethyl-Phenyl)-1-(4,6-Dimethyl-Pyrimidin-2-YL)-1H-Pyrrolo[2,3-c]Pyridine

HRID 472027Notes

Reaction equation

HRID 472027 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][NH:17][C:14]2=[CH:15][N:16]=1)[CH3:2].[H-].[Na+].Cl[C:23]1[N:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[N:24]=1.O>CN(C=O)C.CCOC(C)=O>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][N:17]([C:23]3[N:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[N:24]=3)[C:14]2=[CH:15][N:16]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 205502-Chloro-4,6-dimethylpyrimidineHCID 24758Sodium hydrideHCID 116732465-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 582699465-(2,6-Diethyl-Phenyl)-1-(4,6-Dimethyl-Pyrimidin-2-YL)-1H-Pyrrolo[2,3-c]Pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine (10 mg, 0.04 mmol) in DMF (0.5 mL) is added NaH (95%, 3 mg). The reaction mixture is stirred at room temperature for 30 minutes, and then 2-chloro-4,6-dimethyl-pyrimidine (17 mg, 0.12 mmol)) is added. The mixture is heated at 60° C. overnight and cooled. Water (1 mL) and EtOAc (2 mL) are added to the mixture. The organic layer is separated, washed with water once and concentrated under reduced pressure. The residue is purified by PTLC (Hexane/EtOAc 4:1) to give the titled compound. 1H NMR: (CDCl3) 10.21 (s, 1H), 8.48 (d, 1H), 7.47 (s, 1H), 7.28 (t, 1H), 7.15 (d, 2H), 6.87 (s, 1H), 6.68 (d, 1H), 2.55 (s, 6H), 2.36 (m, 4H), 1.03 (t, 6H).

Workup

  1. temperatureThe mixture is heated at 60° C. overnight
  2. temperaturecooled
  3. customThe organic layer is separated
  4. washwashed with water once
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by PTLC (Hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-3cb85de494f241969c696bd7123f3495
Source dataset
uspto-grants-2014_01
Patent number
US08633193B2

Reaction notes

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