4-Chloro-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazine → 4-(4-Imidazolylethylamino)-2-methylthiopyrazolo(1,5-a)-1,3,5-Triazine

HRID 1285120Notes

Reaction equation

HRID 1285120 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.[NH2:13][CH2:14][CH2:15][C:16]1[N:20]=[CH:19][NH:18][CH:17]=1>CO>[NH:18]1[CH:17]=[C:16]([CH2:15][CH2:14][NH:13][C:2]2[N:7]3[N:8]=[CH:9][CH:10]=[C:6]3[N:5]=[C:4]([S:11][CH3:12])[N:3]=2)[N:20]=[CH:19]1

Participants

4

Reactant 2

HCID 129161154-Chloro-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazineHCID 178419017HCID 178419017, compound

Product 1

HCID 1785034954-(4-Imidazolylethylamino)-2-methylthiopyrazolo(1,5-a)-1,3,5-Triazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 30 mg 4-chloro-2-methylthiopyrazolo(1,5-a)-1,3,5-triazine and 33 mg free histamine in 3 ml of methanol is stirred at room temperature overnight. After evaporation of solvent, the residue is dissolved in ethylacetate, washed with water, and dried over MgSO4. After removal of solvent, the residue is subject to silica gel preparative thin layer chromatography using CHCl3 /methanol=9:1 as a developing solvent. Appropriate fractions are isolated, extracted with CHCl3 /CH3OH (3:1), and solvent removed in vacuo to dryness. 20 mg of a white solid are recovered. TLC (silica gel CHCl3 /CH3OH=3:1) Rf=0.15.

Workup

  1. customAfter evaporation of solvent
  2. dissolutionthe residue is dissolved in ethylacetate
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customAfter removal of solvent
  6. customAppropriate fractions are isolated
  7. extractionextracted with CHCl3 /CH3OH (3:1), and solvent
  8. customremoved in vacuo to dryness
  9. custom20 mg of a white solid are recovered

Sources & evidence

ORD record
ord-34e9b56370cd4382b2ea2e2b55da1fa9
Source dataset
uspto-grants-1986_01
Patent number
US04565815

Reaction notes

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