Methyl iodide → HCID 20718796, compound

HRID 1250704Notes

Reaction equation

HRID 1250704 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)[NH:11][C:10]([O:21][CH3:22])=[N:9][C:8]=1[CH3:23])=[O:6].[CH3:24]I>CN(C=O)C>[CH3:3][O:4][C:5]([C:7]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)[N:11]([CH3:24])[C:10]([O:21][CH3:22])=[N:9][C:8]=1[CH3:23])=[O:6].[CH3:3][O:4][C:5]([C:7]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)[N:11]=[C:10]([O:21][CH3:22])[N:9]([CH3:24])[C:8]=1[CH3:23])=[O:6]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178498444HCID 178498444, compound

Product 2

HCID 20718796HCID 20718796, compoundHCID 20718798HCID 20718798, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of a 60% oil dispersion of NaH (96 mg, 2.2 mmol) in DMF (3 ml) at 0° C. was added a DMF solution (5 ml) of (+6-(3,4-Difluorophenyl)-2-methoxy-4-methyl-1,6-dihydro-pyrimidine-5-carboxylic acid methyl ester (592 mg, 2.0 mmol, [αD]=+28°). After the mixture was stirred 30 min, a DMF solution (2 ml) of methyliodide (312 mg, 2.2 mmol) was added and the reaction stirred at room temperature for 45 min. The DMF was removed in vacuo, the residue treated with water and extracted with ethyl acetate(3X). The extracts were combined, washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give a crude oil (800 mg). Flash chromatography on silica gel (3% to 6% diethyl ether in methylene chloride) gave 6-(3,4-difluorophenyl)-2-methoxy-1,4-dimethyl-1,6-dihydro-pyrimidine-5-carboxylic acid methyl ester and 4-(3,4-difluorophenyl)-2-methoxy-1,6-dimethyl-1,4-dihydro-pyrimidine-5-carboxylic acid methyl ester as colorless oils.

Workup

  1. stirringthe reaction stirred at room temperature for 45 min
  2. customThe DMF was removed in vacuo
  3. additionthe residue treated with water
  4. extractionextracted with ethyl acetate(3X)
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a crude oil (800 mg)

Sources & evidence

ORD record
ord-836fdad8348f4c92af1886e2a0cd0781
Source dataset
uspto-grants-2002_01
Patent number
US06339090B1

Reaction notes

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