Hydrochloric Acid → 4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxylic Acid

HRID 874506Notes

Reaction equation

HRID 874506 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH2:5][O:6][C:7]1[C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][N:10]=[C:9]([S:18][CH3:19])[N:8]=1.[OH-].[Na+].Cl>O.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH2:5][O:6][C:7]1[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=[C:9]([S:18][CH3:19])[N:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71235044Ethyl 4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxylate

Product 1

HCID 712350394-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxylic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxylate (3.0 g, 8.15 mmol) and sodium hydroxide (652 mg, 16.3 mmol) were dissolved in 10 mL of water and 50 mL of THF, reacted at room temperature for 5 h. The diluted hydrochloric acid was added to adjust to pH=6, extraction was performed with dichloromethane (30 mL×3), the extract was dried and concentrated to obtain a white solid, and this product was directly used in the next reaction without purification.

Workup

  1. extractionto adjust to pH=6, extraction
  2. customthe extract was dried
  3. concentrationconcentrated
  4. customto obtain a white solid
  5. customthis product was directly used in the next reaction without purification

Sources & evidence

ORD record
ord-1a16452cb0744949a45bd469c40be444
Source dataset
uspto-grants-2015_03
Patent number
US08980904B2

Reaction notes

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