Water → DL-5 Chloro-6-ethyl-4-(alpha-ethyl-4-acetonyloxybenzyl)aminopyrimidine

HRID 703864Notes

Reaction equation

HRID 703864 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])[C:34]2[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=2)[CH:29]=[C:28]([CH2:43][CH3:44])[N:27]=1.Cl[CH2:46][C:47](=[O:49])[CH3:48].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C.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]([CH2:41][CH3:42])[C:34]2[CH:39]=[CH:38][C:37]([O:40][CH2:46][C:47]([CH3:48])=[O:49])=[CH:36][CH:35]=2)[CH:29]=[C:28]([CH2:43][CH3:44])[N:27]=1

Participants

8

Reactant 4

HCID 962WaterHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 131716268DL-5 Chloro-6-ethyl-4-(alphaethyl-4-hydroxybenzylamino)pyrimidine

Product 1

HCID 131716273DL-5 Chloro-6-ethyl-4-(alpha-ethyl-4-acetonyloxybenzyl)aminopyrimidineYield 39.8%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3.0 g of dl-5-chloro-6-ethyl-4-(α-ethyl-4-hydroxybenzyl)aminopyrimidine dissolved in 30 ml of N,N-dimethylformamide were added 1.2 g of chloroacetone and 1.7 g of anhydrous potassium carbonate, and the mixture was stirred at 80° C. for 8 hours. After completion of the reaction, the reaction mixture was charged into water and the separated oily product was extracted with ethyl acetate. The extract was washed with water, dried with anhydrous sodium sulfate, and then ethyl acetate was distilled off under reduced pressure. The oily product obtained was isolated by column chromatography (Wako Gel C-200, trade name, eluted with toluene:ethyl acetate=7:1) to give 1.3 g of the desired product as pale yellow liquid.

Workup

  1. customAfter completion of the reaction
  2. extractionthe separated oily product was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationethyl acetate was distilled off under reduced pressure
  6. customThe oily product obtained

Sources & evidence

ORD record
ord-9cbdc0db2e91416189d55fe98d5d1109
Source dataset
uspto-grants-1991_01
Patent number
US04985426

Reaction notes

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