Potassium Hydroxide → HCID 19101098, compound

HRID 1588062Notes

Reaction equation

HRID 1588062 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([NH:11][C:12]2[N:17]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:15]([OH:22])=[C:14]([C:23]([CH3:26])([CH3:25])[CH3:24])[N:13]=2)[S:9][CH:10]=1)=[O:5])C.[OH-].[K+]>CO>[CH3:21][C:18]([C:16]1[C:15]([OH:22])=[C:14]([C:23]([CH3:24])([CH3:25])[CH3:26])[N:13]=[C:12]([NH:11][C:8]2[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=2)[N:17]=1)([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54479191HCID 54479191, compound

Product 1

HCID 19101098HCID 19101098, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-([4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]amino)-4-thiazolecarboxylic acid ethyl ester (0.5 g, 1.3 mmol) in 20 mL of methanol is treated with 10 mL of 1.0N KOH (aq) at room temperature. After 3.5 hours, the methanol is removed under reduced pressure, and the aqueous solution is acidified to pH 4 with concentrated HCl. The resulting precipitate is collected by filtration and recrystallized from MeOH/water. Yield of 2-([4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]amino)-4-thiazolecarboxylic acid is 0.09 g (26%); mp 251°-253° C.

Workup

  1. customthe methanol is removed under reduced pressure
  2. filtrationThe resulting precipitate is collected by filtration
  3. customrecrystallized from MeOH/water

Sources & evidence

ORD record
ord-d7cd99ebe7c04590b93d555c3972677f
Source dataset
uspto-grants-1993_06
Patent number
US05220025

Reaction notes

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