Citric Acid → 2,6-Dimethyl-1H-pyrrolo[3,2-d]pyrimidin-4(5H)-one

HRID 1423385Notes

Reaction equation

HRID 1423385 reaction equation
CCO.Cl.C([O:7][C:8]([C:10]1[NH:11][C:12]([CH3:19])=[CH:13][C:14]=1[NH:15][C:16](=[NH:18])[CH3:17])=O)C.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[CH3:17][C:16]1[NH:18][C:8](=[O:7])[C:10]2[NH:11][C:12]([CH3:19])=[CH:13][C:14]=2[N:15]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 178470387HCID 178470387, compound

Product 1

HCID 1357250272,6-Dimethyl-1H-pyrrolo[3,2-d]pyrimidin-4(5H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction flask equipped with a mechanical stirrer and a reflux condenser is charged with EtOH (900 mL), Ethyl-3-(ethanimidoylamino)-5-methyl-1H-pyrrole-2-carboxylate hydrochloride from example A5 (82.79 g; 0.34 mol) and 6M NaOH (226 mL; 1.36 mol). The well-stirred reaction mixture is heated to gentle reflux for 4 hours and is cooled to ambient temperature. The resulting solution is diluted with water (1000 mL) and the pH is adjusted to 6.5 by carefully addition of 2M citric acid. The precipitate is collected by suction filtration, washed with several portions of water and dried in vacuum at 50° C. to yield the title compound as off-white solid.

Workup

  1. customA reaction flask equipped with a mechanical stirrer and a reflux condenser
  2. customThe well-stirred reaction mixture
  3. temperatureis heated
  4. temperatureto gentle reflux for 4 hours
  5. filtrationThe precipitate is collected by suction filtration
  6. washwashed with several portions of water
  7. customdried in vacuum at 50° C.

Sources & evidence

ORD record
ord-350298bcd89b406a86e4197dfd9437ed
Source dataset
uspto-grants-2015_01
Patent number
US08927557B2

Reaction notes

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