Methyl iodide → HCID 20381973, compound

HRID 1763504Notes

Reaction equation

HRID 1763504 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]1[CH:17]=[C:16]2[N:7]([C:8](=[O:19])[N:9]([CH3:18])[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=32)[N:6]=1.[CH3:20]I>C(COC)OC.CN(C)P(=O)(N(C)C)N(C)C>[CH3:20][O:3][CH2:4][C:5]1[CH:17]=[C:16]2[N:7]([C:8](=[O:19])[N:9]([CH3:18])[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=32)[N:6]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20382025HCID 20382025, compound

Product 1

HCID 20381973HCID 20381973, compound

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

To a suspension of 32 mg (0.0013 mole) of oil-free sodium hydride in 25 ml of glyme is added 227 mg (0.001 mole) of 2-(hydroxymethyl)-6-methylpyrazolo[1,5-c]quinazolin-5(6H)-one. The suspension is stirred for 15 minutes and then a solution of 0.66 ml (0.0107 mole) of methyl iodide in 2 ml of hexamethylphosphoric triamide added. The reaction mixture is stirred for 18 hours at room temperature. The solution is filtered and the filtrate stripped to an oil which is partitioned between dichloromethane and aqueous sodium thiosulfate. The organic phase is washed with water and stripped to an oil which is dissolved in acetone and applied to a Merck silica gel plate (20 cm × 20 cm × 2 mm thick). The chromatogram is developed with chloroform-methanol (9:1) and the product is eluted off with acetone. Evaporation of the acetone gives an oil that solidifies on standing under pentane at 5°. The yield of title compound is 100 mg (41%), m.p. 98°-100°.

Workup

  1. stirringThe reaction mixture is stirred for 18 hours at room temperature
  2. filtrationThe solution is filtered
  3. customis partitioned between dichloromethane and aqueous sodium thiosulfate
  4. washThe organic phase is washed with water
  5. dissolutionis dissolved in acetone
  6. washthe product is eluted off with acetone
  7. customEvaporation of the acetone
  8. customgives an oil that
  9. customon standing under pentane at 5°

Sources & evidence

ORD record
ord-540fc81b8f6c45f2ac3ca7df3ddc0751
Source dataset
uspto-grants-1978_09
Patent number
US04112096

Reaction notes

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