4,6-Nonanedione → 4-(5,7-Dipropyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-1-piperazinecarboxylic acid, ethyl ester

HRID 1380521Notes

Reaction equation

HRID 1380521 reaction equation
[NH2:1][C:2]1[NH:3][C:4]([N:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8]2)=[N:5][N:6]=1.[CH3:18][CH2:19][CH2:20][C:21](=O)[CH2:22][C:23](=O)[CH2:24][CH2:25][CH3:26]>C(O)(=O)C>[CH2:20]([C:21]1[CH:22]=[C:23]([CH2:24][CH2:25][CH3:26])[N:6]2[N:5]=[C:4]([N:7]3[CH2:8][CH2:9][N:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:12]3)[N:3]=[C:2]2[N:1]=1)[CH2:19][CH3:18]

Participants

4

Reactant 2

HCID 264544,6-NonanedioneHCID 1784733584-(5-amino-4H-1,2,4-triazol-3-yl)-1-piperazinecarboxylic acid, ethyl ester

Product 1

HCID 136860144-(5,7-Dipropyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-1-piperazinecarboxylic acid, ethyl esterYield 93.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4.48 g (0.02 moles) of 4-(5-amino-4H-1,2,4-triazol-3-yl)-1-piperazinecarboxylic acid, ethyl ester, 3.12 g (0.02 moles) of 4,6-nonanedione and 50 ml of glacial acetic acid was refluxed for 12 hours. The resulting solution was evaporated to dryness in vacuo. The residue was partitioned and treated as described in Example 12 and gave 6.77 g of the desired product as colorless crystals, mp 130°-132° C.

Workup

  1. temperaturewas refluxed for 12 hours
  2. customThe resulting solution was evaporated to dryness in vacuo
  3. customThe residue was partitioned
  4. additiontreated

Sources & evidence

ORD record
ord-be58f9a26e5748d680e52bd587380267
Source dataset
uspto-grants-1986_04
Patent number
US04582833

Reaction notes

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