Water → 4-[(4-Methylpyridin-2-yl)methylthio]-quinazoline

HRID 1761862Notes

Reaction equation

HRID 1761862 reaction equation
C[O-].[Na+].[SH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][N:6]=1.Cl.Cl[CH2:17][C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][N:19]=1.O>CO>[CH3:24][C:22]1[CH:21]=[CH:20][N:19]=[C:18]([CH2:17][S:4][C:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=[CH:7][N:6]=2)[CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10942334Sodium MethoxideHCID 200610712-(Chloromethyl)-4-methylpyridine hydrochlorideHCID 178527884HCID 178527884, compound

Product 1

HCID 144799114-[(4-Methylpyridin-2-yl)methylthio]-quinazolineYield 22.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

13 ml of 28% methanolic solution of sodium methoxide were added to a solution of 5.0 g of 4-mercaptoquinazoline and 5.5 g of 2-chloromethyl-4-methylpyridine hydrochloride in 50 ml of methanol and stirred at room temperature for 5 hours. A reaction solution was poured into water and extracted with chloroform. The chloroform layer was washed with an aqueous sodium carbonate solution, dried over sodium sulfate and distilled off under reduced pressure. The residue was purified by silica gel column chromatography. The fraction eluted with 10% ethyl acetate/chloroform was crystallized from isopropyl ether to obtain 1.84 g (22.3%) of the title compound.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform layer was washed with an aqueous sodium carbonate solution
  3. dry with materialdried over sodium sulfate
  4. distillationdistilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. washThe fraction eluted with 10% ethyl acetate/chloroform
  7. customwas crystallized from isopropyl ether

Sources & evidence

ORD record
ord-015a9992a3084f7e9c32d78d87080035
Source dataset
uspto-grants-1989_05
Patent number
US04829069

Reaction notes

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