Water → 6-chloro-2,5-dimethyl-1H-pyrimidin-4-one

HRID 2290614Notes

Reaction equation

HRID 2290614 reaction equation
[OH2:1].[Cl:2][C:3]1[C:8]([CH3:9])=[C:7](Cl)[N:6]=[C:5]([CH3:11])[N:4]=1.[OH-].[Na+].[Cl-].[Na+]>S(=O)(=O)(O)O>[CH3:11][C:5]1[N:6]=[C:7]([OH:1])[C:8]([CH3:9])=[C:3]([Cl:2])[N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 2370134,6-Dichloro-2,5-dimethylpyrimidine

Product 1

HCID 1784334526-chloro-2,5-dimethyl-1H-pyrimidin-4-oneYield 94%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of water (5.6 mL) in sulfuric acid (21 mL) at 20° C. was added the 4,6-dichloro-2,5-dimethylpyrimidine (9.3 g, 52.5 mmol). The reaction mixture was stirred for 2 hours at 23° C. and then poured onto ice to which sodium hydroxide (16 g, 400 mmol) had been added. When the ice melted, sodium chloride (60 g) was dissolved in the solution which was then extracted with ethyl acetate. The combined ethyl acetate extracts were dried, filtered, and concentrated in vacuo to afford 7.8 g (94%) of product as a fluffy white solid. The recrystallization of the product from ethanol provided an analytically pure sample, m.p. 224°-225° C.

Workup

  1. additionhad been added
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe combined ethyl acetate extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a7913ee1925a4e36948ce28edba29f8d
Source dataset
uspto-grants-1986_10
Patent number
US04617393

Reaction notes

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