Methyl iodide → HCID 58423762, compound

HRID 1408761Notes

Reaction equation

HRID 1408761 reaction equation
[H-].[Na+].[NH2:3][C:4]1[NH:8][C:7]2([C:17]3[C:12](=[CH:13][CH:14]=[C:15]([Br:18])[CH:16]=3)[O:11][C:10]([CH3:20])([CH3:19])[CH2:9]2)[C:6](=[O:21])[N:5]=1.[CH3:22]I>C1COCC1>[NH2:3][C:4]1[N:5]([CH3:22])[C:6](=[O:21])[C:7]2([C:17]3[C:12](=[CH:13][CH:14]=[C:15]([Br:18])[CH:16]=3)[O:11][C:10]([CH3:19])([CH3:20])[CH2:9]2)[N:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178423433HCID 178423433, compound

Product 1

HCID 58423762HCID 58423762, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (5.3 mg, 0.131 mmol) is added to a solution of 2′-amino-6-bromo-2,2-dimethyl-spiro[chroman-4,4′-imidazol]-5′(3′H)-one (45 mg, 0.131 mmol) in THF (3 mL) at 0° C. under N2. The mixture is stirred for 1 h at room temperature. Then MeI (18.6 mg, 0.131 mmol) is added. The mixture is quenched with water and extracted with ethyl acetate. The organic layer is concentrated in vacuo. The residue is purified by preparative TLC to give 2′-amino-6-bromo-1′,2,2-trimethylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (40 mg, 80%).

Workup

  1. customThe mixture is quenched with water
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layer is concentrated in vacuo
  4. customThe residue is purified by preparative TLC

Sources & evidence

ORD record
ord-d3be12240e434623b40ab1bcb928f47e
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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