Water → HCID 20437849, compound

HRID 1979994Notes

Reaction equation

HRID 1979994 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][C:6]1[C:7]2[N:8]([N:19]=[CH:20][N:21]=2)[C:9]([NH2:18])=[N:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2].IC.[CH3:24]C(C)([O-])C.[K+].O>C(O)(C)(C)C>[CH3:24][NH:18][C:9]1[N:8]2[N:19]=[CH:20][N:21]=[C:7]2[C:6]([CH2:5][CH2:4][O:3][CH2:1][CH3:2])=[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 55784BemitradineHCID 23665647Potassium tert-butoxide

Product 1

HCID 20437849HCID 20437849, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 3.0 g (0.01 mole) of 8-(2-ethoxyethyl)-7-phenyl-1,2,4-triazolo[2,3-c]pyrimidine-5-amine, ca. 3 g of iodomethane, and ca. 1 g of potassium t-butoxide in t-butyl alcohol was stirred with heating for five hours. The solution was cooled to room temperature and then poured into 200 ml of cold water and extracted with several portions of ethyl acetate. The organic phase was washed with aqueous sodium chloride, dried over sodium sulfate, filtered, and concentrated in vacuo to dryness. Column chromatography on silica gel afforded 175 mg of the title monomethylated product.

Workup

  1. temperaturewith heating for five hours
  2. extractionextracted with several portions of ethyl acetate
  3. washThe organic phase was washed with aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to dryness
  7. customColumn chromatography on silica gel afforded 175 mg of the title monomethylated product

Sources & evidence

ORD record
ord-e8cdef659d3a49d7b1842a6a1b975763
Source dataset
uspto-grants-1984_11
Patent number
US04483987

Reaction notes

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