Water → DL-5 Chloro-4-(alpha-ethyl-3-phenoxybenzylamino)-6-methylthiomethylpyrimidine

HRID 330310Notes

Reaction equation

HRID 330310 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]([CH2:47][CH3:48])[C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([O:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:35]=2)[CH:29]=[C:28]([CH2:49]Cl)[N:27]=1.[Na].[CH3:52][SH:53].O.C1(C)C=CC=CC=1>CO.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]([CH2:47][CH3:48])[C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([O:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:35]=2)[CH:29]=[C:28]([CH2:49][S:53][CH3:52])[N:27]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 45051789Methylmercaptan sodiumHCID 131716257DL-5 Chloro-6-chloromethyl-4-(alpha-ethyl-3-phenoxybenzyl)aminopyrimidine

Product 1

HCID 131716255DL-5 Chloro-4-(alpha-ethyl-3-phenoxybenzylamino)-6-methylthiomethylpyrimidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2.0 g of dl-5-chloro-6-chloromethyl-4-(α-ethyl-3-phenoxybenzyl)aminopyrimidine obtained in Example 4 dissolved in 50 ml of methanol was added 10 ml of a 15% aqueous methanthiol sodium salt solution, and the mixture was refluxed under stirring for 2 hours. After completion of the reaction, the product was poured into water and extracted with ethyl acetate. 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 chromatography (Wako Gel C-200, trade name, eluted with toluene:ethyl acetate=5:1) to give 1.8 g of the desired product as pale yellow oily liquid.

Workup

  1. temperaturethe mixture was refluxed
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe 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-5e85b2df28114c38ad359e28446850a2
Source dataset
uspto-grants-1990_01
Patent number
US04895849

Reaction notes

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