Methyl iodide → HCID 19357218, compound

HRID 377793Notes

Reaction equation

HRID 377793 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]([CH2:18][C:19]2[N:23]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][CH:26]=3)[CH:22]=[N:21][CH:20]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:11])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].IC.[CH3:37]COC(C)=O.CCCCCC>CN(C=O)C.O>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([N:9]([CH3:37])[C:10]([N:12]([CH2:18][C:19]2[N:23]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([C:31]#[N:32])=[CH:29][CH:30]=3)[CH:22]=[N:21][CH:20]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9890963HCID 9890963, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 19357218HCID 19357218, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of urea 1 (remaining half of crude product prepared above) in 1 mL of dry DMF at 0° C. was added NaH (14 mg, 60% dispersion in mineral oil). After 15 minutes, iodomethane (0.029 mL) was added dropwise. The reaction was stirred at 0° C. for four hours, then poured into EtOAc/hexane (2:1) and water, washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide a purple oil. This material was purified by silica gel chromatography (2-5% MeOH/CH2Cl2), taken up in CH2Cl2 and treated with 1 M HCl/ether solution, and concentrated in vacuo. The product hydrochloride 8 (22 mg) was isolated as a yellow solid.

Workup

  1. washwashed with sat. aq. NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide a purple oil
  6. customThis material was purified by silica gel chromatography (2-5% MeOH/CH2Cl2)
  7. additiontreated with 1 M HCl/ether solution
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c04ce97eb2834966b0e417756178c912
Source dataset
uspto-grants-2000_02
Patent number
US06028201

Reaction notes

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