Hydrochloric Acid → DL-5 Chloro-6-ethyl-4-[alpha-ethyl-4-(2-methoxyiminoethoxy)benzyl]aminopyrimidine

HRID 330319Notes

Reaction equation

HRID 330319 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]([CH2:49][CH3:50])[C:34]2[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH:42](OCC)OCC)=[CH:36][CH:35]=2)[CH:29]=[C:28]([CH2:51][CH3:52])[N:27]=1.Cl.[CH3:54][O:55][NH2:56].Cl.C1(C)C=CC=CC=1>C(O)C.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:25][C:26]1[N:31]=[C:30]([NH:32][CH:33]([CH2:49][CH3:50])[C:34]2[CH:35]=[CH:36][C:37]([O:40][CH2:41][CH:42]=[N:56][O:55][CH3:54])=[CH:38][CH:39]=2)[CH:29]=[C:28]([CH2:51][CH3:52])[N:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 521874O-Methylhydroxylamine hydrochlorideHCID 131716277DL-5 Chloro-6-ethyl-4-[alpha-ethyl-4-(2,2-diethoxyethoxy)benzyl]aminopyrimidine

Product 1

HCID 131716279DL-5 Chloro-6-ethyl-4-[alpha-ethyl-4-(2-methoxyiminoethoxy)benzyl]aminopyrimidineYield 42.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1.0 g of dl-5-chloro-6-ethyl-4-[α-ethyl-4-(2,2-diethoxyethoxy)benzyl]aminopyrimidine obtained in Example 19 dissolved in 40 ml of ethanol was added 0.4 g of methoxyamine hydrochloride. Then, after addition of a catalytic amount of a 6N hydrochloric acid, the mixture was stirred at 60° C. for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and extracted with ethyl acetate. Then, the extract was washed with water, dried over anhydrous sodium sulfate and the solvent 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 0.4 g of the desired product as pale yellow liquid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. extractionextracted with ethyl acetate
  4. washThen, the extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe oily product obtained

Sources & evidence

ORD record
ord-364c374efda24f4e87e4106fd11f4050
Source dataset
uspto-grants-1990_01
Patent number
US04895849

Reaction notes

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