Ethanol → 7-Methyl-8-propyl-[1,2,4]triazolo[1,5-C]pyrimidine

HRID 916660Notes

Reaction equation

HRID 916660 reaction equation
[CH2:1]([C:4]1[C:5](Cl)=[N:6][CH:7]=[N:8][C:9]=1[CH3:10])[CH2:2][CH3:3].O.[NH2:13][NH2:14].[CH3:15]CO>>[CH3:10][C:9]1[N:8]=[CH:7][N:13]2[N:14]=[CH:15][N:6]=[C:5]2[C:4]=1[CH2:1][CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 223131564-Chloro-6-methyl-5-propylpyrimidine

Product 1

HCID 534715537-Methyl-8-propyl-[1,2,4]triazolo[1,5-C]pyrimidine

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-6-methyl-5-propyl-pyrimidine (101) (500 mg, 2.93 mmol) and hydrazine monohydrate (880 mg, 17.6 mmol) in EtOH (15 mL) is heated in a sealed tube at 100° C. overnight. On cooling, the solvent is removed and to the residue is added water (15 mL). The solid is filtered and washed with water (5 mL) and ether (10 mL). The solid is then heated in acetic acid (10 mL) in a sealed tube at 110° C. overnight. The excess acetic acid is removed under vacuum. The residue is neutralized with aqueous sodium bicarbonate and then extracted with ethyl acetate. On drying, the solvent is removed to give the product (168).

Workup

  1. temperatureOn cooling
  2. customthe solvent is removed and to the residue
  3. additionis added water (15 mL)
  4. filtrationThe solid is filtered
  5. washwashed with water (5 mL) and ether (10 mL)
  6. temperatureThe solid is then heated in acetic acid (10 mL) in a sealed tube at 110° C. overnight
  7. customThe excess acetic acid is removed under vacuum
  8. extractionextracted with ethyl acetate
  9. customOn drying
  10. customthe solvent is removed

Sources & evidence

ORD record
ord-de45d286aad448c68137effb4b2a52f1
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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