Methyl iodide → HCID 66977074, compound

HRID 712197Notes

Reaction equation

HRID 712197 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]2[C:14]([O:16]CC)=[O:15])=[N:6][CH:7]=1.[H-].[Na+].CI.[CH3:23]CCCCC>C1COCC1>[Br:1][C:2]1[CH:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2([CH3:23])[C:14]([OH:16])=[O:15])=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8058HexaneHCID 24758Sodium hydrideHCID 66977004HCID 66977004, compound

Product 1

HCID 66977074HCID 66977074, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold solution of ethyl 1-(5-bromopyrimidin-2-yl)piperidine-2-carboxylate (0.37 g, 1.18 mmol) in THF (25 mL) was added NaH (60% dispersion in mineral oil, 0.06 g, 1.41 mmol) portion wise. The mixture was stirred at the same temperature for 45 min followed by addition of MeI (0.52 mL, 8.26 mmol) at 0° C. The temperature of the reaction was slowly raised up to rt and left to stir for 16 h. The reaction was then cooled to 0° C., quenched by drop wise addition of ice-cold water then extracted with EtOAc (3×100 mL). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude residue was purified over 100-200 M silica-gel by using 2% EtOAc: hexane to obtain the desired product as off-white solid (0.115 g, 32% yield). MS: 300.09 [M+H]+.

Workup

  1. waitleft
  2. stirringto stir for 16 h
  3. temperatureThe reaction was then cooled to 0° C.
  4. customquenched by drop wise addition of ice-cold water
  5. extractionthen extracted with EtOAc (3×100 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude residue was purified over 100-200 M silica-gel

Sources & evidence

ORD record
ord-d19fd3c1289e4f73933128d4163993d5
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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