Potassium Bicarbonate → 2-(4,6-Dimethoxypyrimidin-2-yl)-2-hydroxy N-methanesulfonyl-2-phenylacetamide

HRID 1451160Notes

Reaction equation

HRID 1451160 reaction equation
Cl[C:2]([C:16]1[N:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[N:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([NH:5][S:6]([CH3:9])(=[O:8])=[O:7])=[O:4].C(=O)(O)[O-:27].[K+]>O>[CH3:25][O:24][C:18]1[CH:19]=[C:20]([O:22][CH3:23])[N:21]=[C:16]([C:2]([OH:27])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]([NH:5][S:6]([CH3:9])(=[O:8])=[O:7])=[O:4])[N:17]=1

Participants

4

Reactant 2

HCID 516893Potassium BicarbonateHCID 199739322-Chloro-2-(4,6-dimethoxypyrimidin-2-yl)-N-methanesulfonyl-2-phenylacetamide

Product 1

HCID 199739352-(4,6-Dimethoxypyrimidin-2-yl)-2-hydroxy N-methanesulfonyl-2-phenylacetamideYield 94.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chloro-2-(4,6-dimethoxypyrimidin-2-yl)-N-methanesulfonyl-2-phenylacetamide (0.5 g) was stirred at room temperature with potassium bicarbonate (0.2 g) in water (10 ml) for 2 hours, by which time all was in solution. After standing for 3 days, the solution was washed with ether (twice) and acidified with hydrochloric acid. Ether extraction (3 times), washing with water (twice), drying over magnesium sulfate and evaporation under vacuum gave 0.45 g of the desired product as a yellow glass. This glass slowly crystallised to a solid, mp 94°-6° C.

Workup

  1. washthe solution was washed with ether (twice) and
  2. extractionEther extraction (3 times)
  3. washwashing with water (twice),
  4. dry with materialdrying over magnesium sulfate and evaporation under vacuum

Sources & evidence

ORD record
ord-03d39270d741449ab7d1b821e5d63e23
Source dataset
uspto-grants-1997_02
Patent number
US05604181

Reaction notes

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