Guanidine → HCID 178430120, compound

HRID 1792826Notes

Reaction equation

HRID 1792826 reaction equation
CO[C:3]([C:5]1[C:9]([CH3:10])=[CH:8][N:7]([C:11]2[N:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:6]=1)=[O:4].[NH2:17][C:18]([NH2:20])=[NH:19]>CN1C(=O)CCC1.O>[CH3:10][C:9]1[C:5]([C:3]([NH:19][C:18]([NH2:20])=[NH:17])=[O:4])=[CH:6][N:7]([C:11]2[N:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:8]=1

Participants

5

Reactant 2

HCID 3520GuanidineHCID 69658291Methyl 4-methyl-1-(pyrimidin-2-yl)-1H-pyrrole-3-carboxylate

Product 1

HCID 178430120HCID 178430120, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

250 mg 4-methyl-1-pyrimidin-2-yl-1H-pyrrole-3-carboxylic acid methyl ester was dissolved in 0.3 mL of NMP. After addition of 1 g guanidine (preparation according to known literature) the mixture was heated under argon for 1 h to 90° C. Completion of the reaction was checked by LCMS. The mixture was cooled to room temperature and then diluted with water, followed by extraction with ethyl acetate. The organic layer was washed with water (twice), dried over anhydrous sodium sulfate. After filtration the solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column flash chromatography (eluent: dichloromethane/methanol=5/1) to obtain 150 mg of N-(4-methyl-1-pyrimidin-2-yl-1H-pyrrole-3-carbonyl)-guanidine.

Workup

  1. temperaturewas heated under argon for 1 h to 90° C
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water (twice),
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration the solvent
  6. distillationwas distilled off under reduced pressure
  7. customthe resulting residue was purified by a silica gel column flash chromatography (eluent: dichloromethane/methanol=5/1)

Sources & evidence

ORD record
ord-12e788a19bb94873a9b8a0a69a0fa889
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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