Sodium Hydroxide → 4-(Isopropylamino)-2-(methylthio)pyrimidine-5-carboxylic Acid

HRID 1783554Notes

Reaction equation

HRID 1783554 reaction equation
[CH:1]([NH:4][C:5]1[C:10]([C:11]([O:13]CC)=[O:12])=[CH:9][N:8]=[C:7]([S:16][CH3:17])[N:6]=1)([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C.O>[CH:1]([NH:4][C:5]1[C:10]([C:11]([OH:13])=[O:12])=[CH:9][N:8]=[C:7]([S:16][CH3:17])[N:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10491237HCID 10491237, compound

Product 1

HCID 127840854-(Isopropylamino)-2-(methylthio)pyrimidine-5-carboxylic AcidYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 5.0 g (19.6 mmol) of ethyl 4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxylate in 20 mL of ethanol is added a solution of 0.8 g (20.6 mmol) of sodium hydroxide in 30 mL of water. The reaction suspension is stirred at room temperature overnight. The reaction solution is diluted with 100 mL of water and washed twice with diethyl ether. The aqueous phase is neutralized with 20.6 mL of 1N HCl. The precipitate is filtered and washed twice with water, dried under vacuum at 70° C. to give 4.0 g (90%) of the title compound: mp 202-203° C. (dec).

Workup

  1. washwashed twice with diethyl ether
  2. filtrationThe precipitate is filtered
  3. washwashed twice with water
  4. customdried under vacuum at 70° C.

Sources & evidence

ORD record
ord-fe62e3f1d3e445e1a47193d0675cf0e7
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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