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

HRID 703866Notes

Reaction equation

HRID 703866 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].[Na].[Cl:26][C:27]1[N:32]=[C:31]([NH:33][CH:34]([CH2:42][CH3:43])[C:35]2[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=2)[CH:30]=[C:29]([CH2:44][CH3:45])[N:28]=1.[CH2:46]([O:48][CH:49]([O:52][CH2:53][CH3:54])[CH2:50]Br)[CH3:47].O.C1(C)C=CC=CC=1>CN(C)C=O.C(OCC)(=O)C>[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:26][C:27]1[N:32]=[C:31]([NH:33][CH:34]([CH2:42][CH3:43])[C:35]2[CH:40]=[CH:39][C:38]([O:41][CH2:50][CH:49]([O:52][CH2:53][CH3:54])[O:48][CH2:46][CH3:47])=[CH:37][CH:36]=2)[CH:30]=[C:29]([CH2:44][CH3:45])[N:28]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 131716264DL-5 Chloro-6-ethyl-4-(alpha-ethyl-4-hydroxybenzyl)aminopyrimidine sodium salt

Product 1

HCID 131716277DL-5 Chloro-6-ethyl-4-[alpha-ethyl-4-(2,2-diethoxyethoxy)benzyl]aminopyrimidineYield 40.3%

Reagents, catalysts & solvents 2

HCID 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-744865b898554d8bb390a61378473427
Source dataset
uspto-grants-1991_01
Patent number
US04985426

Reaction notes

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