Water → DL-5 Chloro-6-ethyl-4-[alpha-ethyl-4-(2,2-diethoxyethoxy)benzyl]aminopyrimidine

HRID 330318Notes

Reaction equation

HRID 330318 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.[Na].[CH2:46]([O:48][CH:49]([O:52][CH2:53][CH3:54])[CH2:50]Br)[CH3:47].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][CH2:50][CH:49]([O:52][CH2:53][CH3:54])[O:48][CH2:46][CH3:47])=[CH:36][CH:35]=2)[CH:29]=[C:28]([CH2:43][CH3:44])[N:27]=1

Participants

8

Reactant 4

HCID 962WaterHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 5360545SodiumHCID 131716268DL-5 Chloro-6-ethyl-4-(alphaethyl-4-hydroxybenzylamino)pyrimidine

Product 1

HCID 131716277DL-5 Chloro-6-ethyl-4-[alpha-ethyl-4-(2,2-diethoxyethoxy)benzyl]aminopyrimidineYield 38.8%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5.0 g of dl-5-chloro-6-ethyl-4-(α-ethyl-4-hydroxybenzyl)aminopyrimidine.sodium salt dissolved in 50 ml of N,N-dimethylformamide was added 4.8 g of bromoacetaldehyde diethylacetal, 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 2.3 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-ed70ba8423964f108db04cc5b3e9c130
Source dataset
uspto-grants-1990_01
Patent number
US04895849

Reaction notes

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