Imidazole → HCID 131716410, compound

HRID 2106786Notes

Reaction equation

HRID 2106786 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]([CH2:44][CH3:45])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][O:40][C:41](Cl)=[O:42])[CH:29]=[C:28]([CH2:46][CH3:47])[N:27]=1.C(N(CC)CC)C.[NH:55]1[CH:59]=[CH:58][N:57]=[CH:56]1>C1(C)C=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]([CH2:44][CH3:45])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][O:40][C:41]([N:55]2[CH:59]=[CH:58][N:57]=[CH:56]2)=[O:42])[CH:29]=[C:28]([CH2:46][CH3:47])[N:27]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 8471TriethylamineHCID 131716412HCID 131716412, compound

Product 1

HCID 131716410HCID 131716410, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 20 ml of toluene was dissolved 1.00 g of dl-5-chloro-6-ethyl-4-[1-ethyl-7-(chlorocarbonyloxy)heptyl]aminopyrimidine, and 0.50 g of triethylamine and 0.22 g of imidazole were added to the solution and the mixture was stirred at room temperature for one hour. After completion of the reaction, the reaction mixture was filtered, and excessive triethylamine 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=3:1) to give 0.80 g of the title compound as pale yellow oily product. nD21.9 1.5332.

Workup

  1. additionwere added to the solution
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered
  4. customexcessive triethylamine and the solvent was removed under reduced pressure
  5. customThe resulting oily product was isolated through a column chromatography (Wako gel C-200, trade name, eluent; toluene:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-deaed9644873479ea20b6cfcb36fdf99
Source dataset
uspto-grants-1990_06
Patent number
US04931455

Reaction notes

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