Methyl iodide → HCID 59363826, compound

HRID 1430644Notes

Reaction equation

HRID 1430644 reaction equation
[CH:1]([N-]C(C)C)(C)C.C([Li])CCC.[CH3:13][O:14][C:15](=[O:27])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1.CN1CCCN(C)C1=O.IC>C1COCC1.O>[CH3:13][O:14][C:15](=[O:27])[CH:16]([C:17]1[CH:18]=[CH:19][C:20]([S:23]([CH3:26])(=[O:24])=[O:25])=[CH:21][CH:22]=1)[CH3:1]

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 5062348DiisopropylamideHCID 16640928Methyl 2-(4-(methylsulfonyl)phenyl)acetateHCID 178418339Butyllithium

Product 1

HCID 59363826HCID 59363826, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of diisopropylamide (0.46 g, 4.56 mmol) in THF (10 ml) was added n-Butyl lithium (3 ml of 1.6 M, 4.80 mmol) drop wise at −78° C. in nitrogen atmosphere and stirred for 30 minutes, to this slowly added solution of (4-Methanesulfonyl-phenyl)-acetic acid methyl ester (1.0 g, 4.38 mmol) and 1,3 dimethyl 3,4,5,6-tetrahydro-2-pyrimidone (3.17 g, 27.75 mmol), stirred for 1 hour at −78° C., followed by drop wise addition of solution of iodomethane in THF (1.14 g, 8.03 mmol in 10 ml) and stirred at the same temperature for one hour. Reaction mixture was allowed to come at RT and stirred for overnight. The reaction mixture was then poured into water (40 ml) under stirring, THF was removed under reduced pressure, and residue was extracted with ethyl acetate (2×25 ml), organic layer was washed with water (2×20 ml), dried over sodium sulfate and solvent was removed under reduced pressure to get oily residue which was purified by column chromatography over silica gel (100-200 mesh), using 50% ethyl acetate in hexanes as an eluent to afford 2-(4-Methanesulfonyl-phenyl)-propionic acid methyl ester (0.94 g, 88.5%) as white solid. 1H NMR (400 MHz, CDCl3): δ 1.54 (d, J=7.2 Hz, 3H), 3.06 (s, 3H), 3.69 (s, 3H), 3.83 (q, J=7.2 Hz, 1H), 7.51 (d, J=8.4 Hz, 2H), 7.90 (d, J=8.4 Hz, 2H), 2-Bromo-2-(4-methanesulfonyl-phenyl)-propionic acid methyl ester (O1-III)

Workup

  1. stirringstirred at the same temperature for one hour
  2. customReaction mixture
  3. customto come at RT
  4. stirringstirred for overnight
  5. stirringunder stirring
  6. customTHF was removed under reduced pressure, and residue
  7. extractionwas extracted with ethyl acetate (2×25 ml), organic layer
  8. washwas washed with water (2×20 ml)
  9. dry with materialdried over sodium sulfate and solvent
  10. customwas removed under reduced pressure
  11. customto get oily residue which
  12. customwas purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-7258197f866546219de964346f496972
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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