Methyl iodide → HCID 52933898, compound

HRID 1843120Notes

Reaction equation

HRID 1843120 reaction equation
[O:1]=[C:2]1[NH:10][C:9]2[C:4](=[N:5][C:6]([C:11]3[CH:12]=[N:13][N:14]4[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][C:15]=34)=[N:7][CH:8]=2)[N:3]1[CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.[CH3:28]I>CN(C=O)C.[H-].[Na+]>[CH3:28][N:10]1[C:9]2[C:4](=[N:5][C:6]([C:11]3[CH:12]=[N:13][N:14]4[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][C:15]=34)=[N:7][CH:8]=2)[N:3]([CH:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[C:2]1=[O:1]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 52933409HCID 52933409, compound

Product 1

HCID 52933898HCID 52933898, compoundYield 102.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24758Sodium hydrideSolvent

Procedure

To a solution of example 1 (48 mg, 0.13 mmol) in DMF (6 mL), 55-65% NaH dispersion in mineral oil (7.3 mg, 0.18 mmol) was added and the resulting solution was stirred at room temperature for 10 min. Then MeI (0.015 mL, 0.25 mmol) was added and the reaction mixture was stirred for 15 h at room temperature. The reaction mixture was quenched with saturated NaCl aqueous solution (10 mL) and extracted with EtOAc (3×10 mL) and CH2Cl2 (2×10 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered and concentrated. The crude product thus obtained was chromatographed over silica gel using MeOH/CH2Cl2 mixtures of increasing polarity as eluent, to afford 50 mg of the desired compound (quantitative yield).

Workup

  1. stirringthe reaction mixture was stirred for 15 h at room temperature
  2. customThe reaction mixture was quenched with saturated NaCl aqueous solution (10 mL)
  3. extractionextracted with EtOAc (3×10 mL) and CH2Cl2 (2×10 mL)
  4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product thus obtained
  8. customwas chromatographed over silica gel
  9. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-5910f1b3761744fc846ce050f13359c7
Source dataset
uspto-grants-2015_02
Patent number
US08946257B2

Reaction notes

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