Sodium Carbonate → 6-(4-Tert-butyl-phenylsulphonylamino)-4-(2-hydroxy-ethoxy)-5-(3-methoxy-phenoxy)-pyrimidine-2-carboxylic acid

HRID 341969Notes

Reaction equation

HRID 341969 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8]1[C:13]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[C:12]([NH:23][S:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[N:11]=[C:10]([C:37]([OH:39])=[O:38])[N:9]=1)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[C:33]([C:30]1[CH:29]=[CH:28][C:27]([S:24]([NH:23][C:12]2[N:11]=[C:10]([C:37]([OH:39])=[O:38])[N:9]=[C:8]([O:7][CH2:6][CH2:5][OH:4])[C:13]=2[O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)(=[O:25])=[O:26])=[CH:32][CH:31]=1)([CH3:36])([CH3:34])[CH3:35]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 572613504-(2-Acetoxy-ethoxy)-6-(4-tert.butyl-phenyl-sulphonylamino)-5-(3-methoxy-phenoxy)-pyrimidine-2-carboxylic acid

Product 1

HCID 442139556-(4-Tert-butyl-phenylsulphonylamino)-4-(2-hydroxy-ethoxy)-5-(3-methoxy-phenoxy)-pyrimidine-2-carboxylic acidYield 40.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

0.09 g of 4-(2-acetoxy-ethoxy)-6-(4-tert.butyl-phenyl-sulphonylamino)-5-(3-methoxy-phenoxy)-pyrimidine-2-carboxylic acid in 4 ml of methanol and 1.5 ml of water was stirred with 0.05 g of sodium carbonate at 20° C. for 2 hours. The methanol was evaporated and the residue was partitioned between chloroform and aqueous 1N hydrochloric acid. The organic phase was dried and evaporated. The residue was purified over silica gel with chloroform-methanol-water, 60:35:5. There was obtained 0.034 g of 6-(4-tert.butyl-phenylsulphonylamino)-4-(2-hydroxy-ethoxy)-5-(3-methoxy-phenoxy)-pyrimidine-2-carboxylic acid, MS: (M-H)- 515.9.

Workup

  1. customThe methanol was evaporated
  2. customthe residue was partitioned between chloroform and aqueous 1N hydrochloric acid
  3. customThe organic phase was dried
  4. customevaporated
  5. customThe residue was purified over silica gel with chloroform-methanol-water, 60:35:5

Sources & evidence

ORD record
ord-34a17c6448d54ade9fbf8ea0c3a61fba
Source dataset
uspto-grants-1999_01
Patent number
US05856484

Reaction notes

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