Triethylamine → HCID 131716408, compound

HRID 2106785Notes

Reaction equation

HRID 2106785 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][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][OH:39])[CH:29]=[C:28]([CH2:40][CH3:41])[N:27]=1.Cl[C:43]([O:45][CH2:46][CH3:47])=[O:44].C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=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][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][O:39][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:29]=[C:28]([CH2:40][CH3:41])[N:27]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 131716406HCID 131716406, compound

Product 1

HCID 131716408HCID 131716408, compoundYield 38.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In 10 ml of dichloromethane were dissolved 0.70 g of dl-5-chloro-6-ethyl-4-(6-hydroxyhexyl)aminopyrimidine and 0.30 g of ethyl chloroformate, and under stirring, 0.40 g of triethylamine and a catalytic amount of 4-dimethylaminopyridine were added to the solution and the mixture was stirred at room temperature for 10 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane and washed with water. Then, 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; toluene:ethyl acetate=4:1) to give 0.30 g of the title compound as pale yellow oily product. nD18.7 1.5138.

Workup

  1. stirringthe mixture was stirred at room temperature for 10 hours
  2. customAfter completion of the reaction
  3. extractionthe reaction mixture was extracted with dichloromethane
  4. washwashed with water
  5. dry with materialThen, the organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe resulting oily product was isolated through a column chromatography (Wako gel C-200, trade name, eluent; toluene:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-1039eab341964c1da0e049b06bfa6e76
Source dataset
uspto-grants-1990_06
Patent number
US04931455

Reaction notes

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