Methyl iodide → HCID 19352599, compound

HRID 378189Notes

Reaction equation

HRID 378189 reaction equation
[CH2:1]([O:12][C:13]1[CH:14]=[N:15][C:16]([C:19]2[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[CH2:27][CH2:28][CH2:29][CH:30]([OH:32])[CH3:31])=[CH:21][CH:20]=2)=[N:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH3:33]I>[Ag]=O.C(Cl)(Cl)Cl>[CH2:1]([O:12][C:13]1[CH:14]=[N:15][C:16]([C:19]2[CH:20]=[CH:21][C:22](/[CH:25]=[CH:26]/[CH2:27][CH2:28][CH2:29][CH:30]([O:32][CH3:33])[CH3:31])=[CH:23][CH:24]=2)=[N:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 19352551HCID 19352551, compound

Product 1

HCID 19352599HCID 19352599, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6212ChloroformSolvent

Procedure

At room temperature, 4.0 g (9 mmol) of the (-)-5-undecyloxy-2-{4-(6-hydroxy-1-trans-heptenyl)-phenyl}-pyrimidine obtained in Example 14, 40 ml of methyl iodide and 6.3 g (27 mmol) of silver oxide were stirred for 40 hours. Then, the reaction mixture was washed with 1 N hydrochloric acid and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Purification of the residue by silica gel column chromatography gave 2.1 g (yield 52%) of (-)-5-undecyloxy-2-{4-(6-methoxy-1-trans-heptenyl)-phenyl}-pyrimidine, [α]D20 =-1.6 (c=1.0, CHCl3).

Workup

  1. washThen, the reaction mixture was washed with 1 N hydrochloric acid and saturated aqueous solution of sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customPurification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-9dc67571be714cfd9467800f99d6529f
Source dataset
uspto-grants-2000_02
Patent number
US06030546

Reaction notes

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