Hydrochloric Acid → 4(1H)-Pyrimidinone, 2-(((2-(dimethylamino)phenyl)methyl)thio)-6-methyl-

HRID 2247849Notes

Reaction equation

HRID 2247849 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[S:8])[NH:5][C:4](=[O:9])[CH:3]=1.[CH3:10][N:11]([CH3:20])[C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14]O.Cl.[OH-].[Na+]>>[CH3:10][N:11]([CH3:20])[C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][S:8][C:6]1[NH:5][C:4](=[O:9])[CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 138325Benzenemethanol, 2-(dimethylamino)-HCID 667493Methylthiouracil

Product 1

HCID 1357442584(1H)-Pyrimidinone, 2-(((2-(dimethylamino)phenyl)methyl)thio)-6-methyl-Yield 43%

Conditions

Temperature
60 °C

Procedure

A mixture containing 0.71 g (5 mmol) of 6-methyl-2-thiouracil, 0.76 g (5 mmol) of 2-dimethylaminobenzyl alcohol (J. Chem. Soc. 1954, 4127) and 5 ml of concentrated hydrochloric acid is stirred at 60° C. for 3 hours, then cooled and made alkaline by adding 5N sodium hydroxide solution under cooling by ice. The mixture is extracted 3 times with 20 ml of chloroform each. After combining the organic phase is washed with sodium carbonate solution and then with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated. The residue is twice recrystallized from ethyl acetate to yield 0.59 g (43%) of the title compound, m.p.: 151°-153° C.

Workup

  1. temperaturecooled
  2. temperatureunder cooling by ice
  3. extractionThe mixture is extracted 3 times with 20 ml of chloroform each
  4. washis washed with sodium carbonate solution
  5. dry with materialwith saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue is twice recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-30f7759752ab486692ab855de71aef7d
Source dataset
uspto-grants-1991_08
Patent number
US05037830

Reaction notes

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