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

HRID 1487247Notes

Reaction equation

HRID 1487247 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[NH:8][C:7]([C:9](OCC)=[O:10])=[C:6]([NH:14][C:15](=[NH:20])[CH2:16][CH2:17][CH2:18][CH3:19])[CH:5]=1.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[CH2:16]([C:15]1[NH:20][C:9](=[O:10])[C:7]2[NH:8][C:4]([CH3:3])=[CH:5][C:6]=2[N:14]=1)[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 178446837HCID 178446837, compound

Product 1

HCID 1369342832-Butyl-6-methyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aqueous sodium hydroxide solution (6M, 138 mL) was added dropwise to a solution of ethyl 5-methyl-3-pentanimidamido-1H-pyrrole-2-carboxylate (58.9 g, 0.2 mol) in ethanol (550 mL) cooled in an ice-bath. The reaction mixture was heated at reflux for 2.5 hours then cooled to room temperature. Water (700 mL) was added and the pH adjusted to pH 6.5 using aqueous citric acid (2M). The resultant mixture was stirred for 45 minutes then filtered and the solid material washed with water. The material was dried in a vacuum oven at 50° C. to give the title compound.

Workup

  1. temperaturecooled in an ice-bath
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 2.5 hours
  4. filtrationthen filtered
  5. washthe solid material washed with water
  6. customThe material was dried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-8dd6092a2b444f0496c066e22e0b8f63
Source dataset
uspto-grants-2016_08
Patent number
US09428512B2

Reaction notes

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