Acetyl chloride → HCID 131716414, compound

HRID 2106787Notes

Reaction equation

HRID 2106787 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][NH2:40])[CH:29]=[C:28]([CH2:43][CH3:44])[N:27]=1.C(N(CC)CC)C.[C:52](Cl)(=[O:54])[CH3:53]>C(Cl)(Cl)Cl>[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][NH:40][C:52](=[O:54])[CH3:53])[CH:29]=[C:28]([CH2:43][CH3:44])[N:27]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 131716416HCID 131716416, compound

Product 1

HCID 131716414HCID 131716414, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 10 ml of chloroform were dissolved 0.55 g of dl-5-chloro-6-ethyl-4-(1-ethyl-7-aminoheptyl)aminopyrimidine and 0.25 g of triethylamine, and under ice cooling, 0.18 g of acetyl chloride was added to the solution and the mixture was stirred for one hour. After completion of the reaction, the reaction mixture was extracted with chloroform. After the organic layer was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure. The resulting oily product was isolated through a column chromatography (Wako gel C-200, trade name, eluent; ethyl acetate) to give 0.20 g of the title compound as pale yellow oily product. nD22.4 1.5296.

Workup

  1. customAfter completion of the reaction
  2. extractionthe reaction mixture was extracted with chloroform
  3. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe resulting oily product was isolated through a column chromatography (Wako gel C-200, trade name, eluent; ethyl acetate)

Sources & evidence

ORD record
ord-956745ca944c43e4a4ec99f981388e58
Source dataset
uspto-grants-1990_06
Patent number
US04931455

Reaction notes

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