Dichloromethane → 2-Chloro-5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidine

HRID 653572Notes

Reaction equation

HRID 653572 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]2[N:14]=[C:15](N)[N:16]=[C:4]2[N:3]=1.N([O-])=O.[Na+].C(OCC)(=O)C.C(Cl)[Cl:29]>Cl.O.C(Cl)Cl.C(OCC)(=O)C>[Cl:29][C:15]1[N:16]=[C:4]2[N:3]=[C:2]([CH3:1])[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:5]2[N:14]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 9757135-Methyl-7-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 198890512-Chloro-5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

To 2.0 g (8.9 mmol) of 5-methyl-7-phenyl-1,2,4triazolo[1,5-a]pyrimidin-2-amine stirring in 25 ml of concentrated hydrochloric acid, 1.2 g (17.4 mmol) of sodium nitrite dissolved in 4.0 ml of water was added dropwise at ambient temperature. After the addition, the reaction suspension was warmed at about 60° for 15 minutes followed by stirring another 10 minutes without heat. Ethyl acetate (150 ml) and excess water were added. The ethyl acetate layer was separated whereby a certain amount of insoluble material present was ignored and the extract washed with water (2X), saturated sodium bicarbonate, brine, dried over magnesium sulfate, and evaporated in vacuo to give a solid residue. Silica gel column chromatography (methylene chloride followed by 10:1 methylene chloride/ethyl acetate) afforded the title compound, m.p. 179°-181° C.

Workup

  1. additionwas added dropwise at ambient temperature
  2. additionAfter the addition
  3. temperaturethe reaction suspension was warmed at about 60° for 15 minutes
  4. temperaturewithout heat
  5. customThe ethyl acetate layer was separated whereby a certain amount of insoluble material present
  6. washthe extract washed with water (2X), saturated sodium bicarbonate, brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customto give a solid residue

Sources & evidence

ORD record
ord-1f4663c575454f6e849cda5b4abc5106
Source dataset
uspto-grants-1992_07
Patent number
US05127936

Reaction notes

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