Methyl iodide → HCID 19352599, compound

HRID 725683Notes

Reaction equation

HRID 725683 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 1N 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 1N 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-92f2835c0e7148f698d9fb4165ede4ba
Source dataset
uspto-grants-1998_01
Patent number
US05707547

Reaction notes

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