Methyl iodide → HCID 20348469, compound

HRID 1701123Notes

Reaction equation

HRID 1701123 reaction equation
[CH2:1]([C:4]1[C:5]([O:20][CH3:21])=[CH:6][C:7]([CH2:11][C:12]2[C:13]([NH2:19])=[N:14][C:15]([NH2:18])=[N:16][CH:17]=2)=[CH:8][C:9]=1[OH:10])[CH:2]=[CH2:3].[OH-].[K+].[CH3:24]I>CO>[CH2:1]([C:4]1[C:9]([O:10][CH3:24])=[CH:8][C:7]([CH2:11][C:12]2[C:13]([NH2:19])=[N:14][C:15]([NH2:18])=[N:16][CH:17]=2)=[CH:6][C:5]=1[O:20][CH3:21])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 20348470HCID 20348470, compound

Product 1

HCID 20348469HCID 20348469, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.43 g. of 6-allyl-α-(2,4-diamino-5-pyrimidyl)-5-methoxy-m-cresol, 5 ml. of 1-N potassium hydroxide and 300 ml. of 40% aqueous methanol was treated with 0.32 ml. of methyl iodide and stirred at room temperature for 48 hours. The methanol was removed by distillation and the residue was extracted with ethyl acetate. Working-up of the ethyl acetate extract yielded 5-(4-allyl-3,5-dimethoxybenzyl)-2,4-diaminopyrimidine of melting point 185°-187° C. (from methanol) in a yield of 75%.

Workup

  1. additionA mixture of 1.43 g
  2. customThe methanol was removed by distillation
  3. extractionthe residue was extracted with ethyl acetate
  4. extractionWorking-up of the ethyl acetate extract

Sources & evidence

ORD record
ord-cd41731d0ec34166a38b5369801475ed
Source dataset
uspto-grants-1980_03
Patent number
US04191758

Reaction notes

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