Potassium Hydroxide → 4-(4-Cyanophenyl)-6-methyl-2-(methylsulfanyl)-1-[3-(trifluoromethyl)phenyl]-1,4-dihydro-5-pyrimidinecarboxylic acid

HRID 230289Notes

Reaction equation

HRID 230289 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]([C:15]([O:17]C)=[O:16])=[C:13]([CH3:19])[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[C:11]([S:30][CH3:31])=[N:10]2)=[CH:5][CH:4]=1)#[N:2].[OH-].[K+]>C1COCC1.C(O)C.O.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[C:14]([C:15]([OH:17])=[O:16])=[C:13]([CH3:19])[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[C:11]([S:30][CH3:31])=[N:10]2)=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 57762469Methyl 4-(4-cyanophenyl)-6-methyl-2-(methylsulfanyl)-1-[3-(trifluoromethyl)-phenyl]-1,4-dihydro-5-pyrimidinecarboxylate

Product 1

HCID 577624284-(4-Cyanophenyl)-6-methyl-2-(methylsulfanyl)-1-[3-(trifluoromethyl)phenyl]-1,4-dihydro-5-pyrimidinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

Methyl 4-(4-cyanophenyl)-6-methyl-2-(methylsulfanyl)-1-[3-(trifluoromethyl)-phenyl]-1,4-dihydro-5-pyrimidinecarboxylate (Example 8; 9.51 g, 21.4 mmol) is dissolved in 175 ml THF/ethanol/water (10:5:1). Potassium hydroxide (3.59 g, 64.1 mmol) is added, and the reaction mixture is stirred overnight. The reaction mixture is diluted with 100 ml of water, and the aqueous phase is washed with diethyl ether. The resulting aqueous phase is acidified to pH 1 with hydrochloric acid, and the resulting precipitate is filtered off, dissolved in ethyl acetate and washed with water. After drying with sodium sulfate, the solvent is removed in vacuo to give the product.

Workup

  1. washthe aqueous phase is washed with diethyl ether
  2. filtrationthe resulting precipitate is filtered off
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialAfter drying with sodium sulfate
  6. customthe solvent is removed in vacuo
  7. customto give the product

Sources & evidence

ORD record
ord-1988d67fd5bc40dca5f27563d9dcc299
Source dataset
uspto-grants-2009_07
Patent number
US07566723B2

Reaction notes

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