Propionic Acid → 2,6-Dimethyl-8-ethyl-1-deazapurine

HRID 2255578Notes

Reaction equation

HRID 2255578 reaction equation
C(O)(=O)CC.[NH4+:6].[OH-].[CH3:8][C:9]1[C:14](NC(=O)CC)=[C:13]([CH3:20])[N:12]=[C:11]([NH:21][C:22](=O)[CH2:23][CH3:24])[CH:10]=1>>[CH3:20][C:13]1[N:12]=[C:11]2[N:21]=[C:22]([CH2:23][CH3:24])[NH:6][C:10]2=[C:9]([CH3:8])[CH:14]=1

Participants

4

Reactant 3

HCID 1032Propionic AcidHCID 14923Ammonium HydroxideHCID 18983251HCID 18983251, compound

Product 1

HCID 98153742,6-Dimethyl-8-ethyl-1-deazapurine

Conditions

Temperature
90 °C

Procedure

To a mixture of 8.44 g of a 55:45 mixture of 2-amino-3-nitro-4,6-dimethylpyridine and 2-amino-5-nitro-4,6-dimethylpyridine in MeOH (1.2 L) was added 10% Pd/C (2.4 g). The reaction vessel was evacuated then purged with H2 at 1 atm. and stirred vigorously for 18 h. Filtration through a celite pad, and concentration gave 6.65 g of a mixture of 2,3-diamino-4,6-dimethylpyridine and 2,5-diamino-4,6-dimethylpyridine as a dark solid. To 5.40 g (39.4 mmol) of this mixture was added propionic acid (8.80 mL, 118 mmol) followed by polyphosphoric acid (100 mL). This stirred mixture was heated to 90° C. for 3 h then to 100° C. for 1 hour. The inside walls of the flask were scraped with a spatula to assist dissolution of the solids. After the reaction was complete, the warm mixture was poured onto 300 g of ice and the mixture was made basic with NH4OH. The mixture was extracted (4×50 mL CH2Cl2), dried (K2CO3) and concentrated to give a mixture of the title compound and 4,6-dimethyl-2,5-bis(propionamido)pyridine. Purification (SiO2, 5% MeOH/EtOAc) gave 1.66 g of the title compound as the slower eluting component.

Workup

  1. dissolutiondissolution of the solids
  2. extractionThe mixture was extracted (4×50 mL CH2Cl2)
  3. dry with materialdried (K2CO3)
  4. concentrationconcentrated
  5. customto give

Sources & evidence

ORD record
ord-3e8516354c2d411699e86af4297cce9d
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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