Ammonium formate → 5-(2-Amino-pyrimidin-4-yl)-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 1968551Notes

Reaction equation

HRID 1968551 reaction equation
Cl.[CH2:2]([O:4][C:5]([C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[N:13]=2)[NH:9][C:8]=1Cl)=[O:6])[CH3:3].C([O-])=O.[NH4+]>CO.[Pd]>[CH2:2]([O:4][C:5]([C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[N:13]=2)[NH:9][CH:8]=1)=[O:6])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 687512455-(2-Amino-pyrimidin-4-yl)-2-chloro-1H-pyrrole-3-carboxylic acid ethyl ester hydrochloride

Product 1

HCID 666782975-(2-Amino-pyrimidin-4-yl)-1H-pyrrole-3-carboxylic acid ethyl esterYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 5-(2-Amino-pyrimidin-4-yl)-2-chloro-1H-pyrrole-3-carboxylic acid ethyl ester hydrochloride (33 g, 0.108 mol) in dry methanol (500 mL), ammonium formate (33 g, 0.523 mol) and 10% Pd/C (3.5 g, 0.0028 mol) were added. The reaction was refluxed for 10 hours. The catalyst was filtered through a pad of Celite rinsing the Celite with dichloromethane (100 mL) and then with methanol (100 mL). The organic fraction was concentrated to small volume (50 mL) diluted with dichloromethane (150 mL) and washed with water (1×200 mL) and the acqueous fraction extracted with dichloromethane (1×200 mL). The organic fractions were combined, dried over sodium sulfate, filtered, and concentered to yield 12.5 g (50%) of the title compound as an light brown solid.

Workup

  1. additionwere added
  2. temperatureThe reaction was refluxed for 10 hours
  3. filtrationThe catalyst was filtered through a pad of Celite
  4. washrinsing the Celite with dichloromethane (100 mL)
  5. concentrationThe organic fraction was concentrated to small volume (50 mL)
  6. additiondiluted with dichloromethane (150 mL)
  7. washwashed with water (1×200 mL)
  8. extractionthe acqueous fraction extracted with dichloromethane (1×200 mL)
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered

Sources & evidence

ORD record
ord-ceb8ae441ceb411ab776c4fbe0990607
Source dataset
uspto-grants-2013_04
Patent number
US08426417B2

Reaction notes

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