Acetic Acid → 2-(5-Methyl-1H-1,2,4-triazol-1-yl)pyrimidine-5-carboxylic acid

HRID 1409728Notes

Reaction equation

HRID 1409728 reaction equation
[NH2:1][NH2:2].C[N:4]([CH:6]=[N:7][C:8](=O)[CH3:9])[CH3:5].[C:11]([OH:14])(=[O:13])C>>[CH3:9][C:8]1[N:2]([C:6]2[N:4]=[CH:5][C:9]([C:11]([OH:14])=[O:13])=[CH:8][N:7]=2)[N:1]=[CH:6][N:7]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 9321HydrazineHCID 567145Acetamide, N-[(dimethylamino)methylidene]-

Product 1

HCID 711127712-(5-Methyl-1H-1,2,4-triazol-1-yl)pyrimidine-5-carboxylic acid

Conditions

Temperature
90 °C

Procedure

2-Chloropyrimidine-5-carboxylic acid (1.5 g) is dissolved in MeOH (25 mL) and hydrazine (5 mL) is added at r.t. An exothermic reaction occurs and a solid precipitate forms. The solid is filtered off washing with a little MeOH and is dried by suction to give the hydrazine intermediate. The hydrazine is dissolved in acetic acid (4 mL) and N-((dimethylamino)methylene)acetamide [made from acetamide and N,N-dimethylformamide-dimethylacetal by procedure in US2007/0111984A1] (2.0 g) is added and heated at 90° C. for 1 h. After cooling and concentrating the residue is purified by HPLC to give the title compound. LC (method 20): tR=1.24 min; Mass spectrum (APCI): m/z=206 [M+H]+.

Workup

  1. temperatureAfter cooling
  2. concentrationconcentrating the residue
  3. customis purified by HPLC

Sources & evidence

ORD record
ord-42a34c4093464b14af4a48e6ea3fd707
Source dataset
uspto-grants-2014_12
Patent number
US08921398B2

Reaction notes

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