Methyl iodide → HCID 131716402, compound

HRID 2106783Notes

Reaction equation

HRID 2106783 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:6]=[CH:5][C:4]=1[OH:24].[Cl:25][C:26]1[N:31]=[C:30]([NH:32][CH:33]([CH2:41][CH3:42])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][OH:40])[CH:29]=[C:28]([CH2:43][CH3:44])[N:27]=1.[H-].[Na+].CI.[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:6]=[CH:5][C:4]=1[OH:24].[Cl:25][C:26]1[N:31]=[C:30]([NH:32][CH:33]([CH2:41][CH3:42])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][O:40][CH3:1])[CH:29]=[C:28]([CH2:43][CH3:44])[N:27]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 131716396HCID 131716396, compound

Product 1

HCID 131716402HCID 131716402, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 20 ml of anhydrous tetrahydrofuran was dissolved 0.56 g of dl-5-chloro-6-ethyl-4-(1-ethyl-7-hydroxyheptyl)aminopyrimidine, and 0.15 g of sodium hydride was added thereto. After stirring at room temperature for 30 minutes, 0.43 g of methyl iodide was added to the mixture, and the mixture was refluxed for 5 hours under stirring. After allowing to stand for cooling, an aqueous ammonium chloride solution was added to the reaction mixture and the reaction mixture was extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure The resulting oily product was isolated through a column chromatography (Wako gel C-200, trade name, eluent; toluene:ethyl acetate=10:1) to give 0.19 g of the title compound as pale yellow oily liquid. nD23.0 1.5094.

Workup

  1. additionwas added
  2. temperaturethe mixture was refluxed for 5 hours
  3. stirringunder stirring
  4. temperaturefor cooling
  5. extractionthe reaction mixture was extracted with ethyl acetate The organic layer
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure The resulting oily product
  8. customwas isolated through a column chromatography (Wako gel C-200, trade name, eluent; toluene:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-79b11df2219b4d7482d000a88255a20d
Source dataset
uspto-grants-1990_06
Patent number
US04931455

Reaction notes

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