Dimethylformamide → 7-Phenyl-8-(prop-2-yn-1-yl)[1,2,4]triazolo[4,3-c]pyrimidin-5-amine

HRID 1995734Notes

Reaction equation

HRID 1995734 reaction equation
Cl[C:2]1[C:7]([CH2:8][C:9]#[CH:10])=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=[C:4]([NH2:17])[N:3]=1.[CH:18]([NH:20][NH2:21])=O.CN(C)C=O>O>[C:11]1([C:6]2[N:5]=[C:4]([NH2:17])[N:3]3[CH:18]=[N:20][N:21]=[C:2]3[C:7]=2[CH2:8][C:9]#[CH:10])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 12229HydrazinecarboxaldehydeHCID 20487936HCID 20487936, compound

Product 1

HCID 204879357-Phenyl-8-(prop-2-yn-1-yl)[1,2,4]triazolo[4,3-c]pyrimidin-5-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.7 Parts of 4-chloro-6-phenyl-5-(2-propynyl)pyrimidin-2-amine and 0.84 part of formylhydrazine are added to 20 parts by volume dimethylformamide containing 2.0 parts of molecular sieve 3A and refluxed under nitrogen for two hours. The solution is allowed to cool and is poured into cold water. The crystalline product is filtered out, washed with water and dried. The product is chromatographed to give 7-phenyl-8-(2-propynyl)-1,2,4-triazolo[4,3-c]pyrimidin-5-amine having the formula: ##STR6##

Workup

  1. temperaturerefluxed under nitrogen for two hours
  2. temperatureto cool
  3. filtrationThe crystalline product is filtered out
  4. washwashed with water
  5. customdried
  6. customThe product is chromatographed

Sources & evidence

ORD record
ord-9ce45766bbde4c05ad3ed4fb7351e6f3
Source dataset
uspto-grants-1983_09
Patent number
US04405780

Reaction notes

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