Sodium hydride → 4-(4-Tert-butyl-phenylsulphonylamino)-5-(3-methoxy-phenoxy)-6-(2-pyrimidin-2-yloxy-ethoxy)-pyrimidine-2-carboxylic acid

HRID 341971Notes

Reaction equation

HRID 341971 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[N:20]=[C:19]([C:21]([OH:23])=[O:22])[N:18]=[C:17]([O:24][CH2:25][CH2:26][OH:27])[C:16]=2[O:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:40]1[N:45]=[CH:44][CH:43]=[CH:42][N:41]=1.[NH4+].[Cl-]>CC(N(C)C)=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[C:16]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=3)=[C:17]([O:24][CH2:25][CH2:26][O:27][C:40]3[N:45]=[CH:44][CH:43]=[CH:42][N:41]=3)[N:18]=[C:19]([C:21]([OH:23])=[O:22])[N:20]=2)(=[O:12])=[O:13])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 744042-ChloropyrimidineHCID 442139556-(4-Tert-butyl-phenylsulphonylamino)-4-(2-hydroxy-ethoxy)-5-(3-methoxy-phenoxy)-pyrimidine-2-carboxylic acid

Product 1

HCID 541549754-(4-Tert-butyl-phenylsulphonylamino)-5-(3-methoxy-phenoxy)-6-(2-pyrimidin-2-yloxy-ethoxy)-pyrimidine-2-carboxylic acidYield 69.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

0.2 g of 6-(4-tert-butyl-phenylsulphonylamino)-4-(2-hydroxy-ethoxy)-5-(3-methoxy-phenoxy)-pyrimidine-2-carboxylic acid in 5 ml of dimethylacetamide was stirred at 20° C. for 3 hours with 0.04 g of sodium hydride and 0.07 g of 2-chloropyrimidine and the mixture was neutralized with saturated NH4Cl solution. The reaction mixture was washed with ethyl acetate. The aqueous phase was adjusted to pH 2 with 1N HCl and extracted with chloroform. The organic phase was dried, the solvent was evaporated and the residue was purified over silica gel with chloroform-methanol-water 60:35:5. There was obtained 0.16 g of 4-(4-tert-butyl-phenylsulphonylamino)-5-(3-methoxy-phenoxy)-6-(2-pyrimidin-2-yloxy-ethoxy)-pyrimidine-2-carboxylic acid, MS: (M+H)+ 596.

Workup

  1. washThe reaction mixture was washed with ethyl acetate
  2. extractionextracted with chloroform
  3. customThe organic phase was dried
  4. customthe solvent was evaporated
  5. customthe residue was purified over silica gel with chloroform-methanol-water 60:35:5

Sources & evidence

ORD record
ord-cc0fe89bc74f45d3bce17bc8bd61be4f
Source dataset
uspto-grants-1999_01
Patent number
US05856484

Reaction notes

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