Sodium Carbonate → HCID 131716400, compound

HRID 2106782Notes

Reaction equation

HRID 2106782 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]O)[CH:29]=[C:28]([CH2:43][CH3:44])[N:27]=1.S(Cl)([Cl:47])=O.C(=O)([O-])[O-].[Na+].[Na+]>N1C=CC=CC=1>[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][Cl:47])[CH:29]=[C:28]([CH2:43][CH3:44])[N:27]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 131716396HCID 131716396, compound

Product 1

HCID 131716400HCID 131716400, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 0.9 g of dl-5-chloro-6-ethyl-4-(1-ethyl-7-hydroxyheptyl)aminopyrimidine and 0.28 g of pyridine was gradually added dropwise 0.42 g of thionyl chloride under cooling to -10° to -5° C. After dropwise addition, the mixture was heated at 60° to 70° C. for one hour and allowed to stand for cooling. The reaction mixture was neutralized with an aqueous sodium carbonate solution and 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 0.55 g of the title compound as pale yellow oily liquid. nD22.8 1.5246.

Workup

  1. temperatureunder cooling to -10° to -5° C
  2. additionAfter dropwise addition
  3. temperaturethe mixture was heated at 60° to 70° C. for one hour
  4. temperaturefor cooling
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe resulting oily product was isolated through a column chromatography (Wako gel C-200, trade name, eluent; toluene:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-ace6ddccb3ec4f68a6782addd7c97b33
Source dataset
uspto-grants-1990_06
Patent number
US04931455

Reaction notes

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