Lithium hydroxide, monohydrate → HCID 17854681, compound

HRID 1727901Notes

Reaction equation

HRID 1727901 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=2)=[N:7][C:8]([S:13][CH3:14])=[N:9][C:10]=1[CH2:11][CH3:12])=[O:4].O.[OH-].[Li+]>C1COCC1.O.C(OCC)(=O)C>[Cl:22][C:17]1[CH:16]=[C:15]([C:6]2[C:5]([C:3]([OH:4])=[O:2])=[C:10]([CH2:11][CH3:12])[N:9]=[C:8]([S:13][CH3:14])[N:7]=2)[CH:20]=[C:19]([Cl:21])[CH:18]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86590783HCID 86590783, compound

Product 1

HCID 17854681HCID 17854681, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

274 mg (0.768 mmol) of 4-(3,5-dichlorophenyl)-6-ethyl-2-(methylthio)-pyrimidine-5-carboxylic acid methylester was dissolved in 5 ml of THF and 5 ml of water. 38.7 mg (0.922 mmol) of lithium hydroxide monohydrate was added and stirred at 80° C. for 12 hours. 10 ml of water was added thereto and the organic layer was batched off. The obtained aqueous layer was diluted with ethyl acetate and washed with 5 ml of 3 N hydrochloric acid and then with 5 ml of saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain the title compound.

Workup

  1. washwashed with 5 ml of 3 N hydrochloric acid
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f34f7e2b65034451ab3c6156da5ac4c9
Source dataset
uspto-grants-2009_02
Patent number
US07494989B2

Reaction notes

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