Tetrahydrofuran → 2-(Dipropylamino)-6-methylpyrimidine-4-carboxylic acid

HRID 14234Notes

Reaction equation

HRID 14234 reaction equation
[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[C:5]1[N:10]=[C:9]([C:11]([O:13]C)=[O:12])[CH:8]=[C:7]([CH3:15])[N:6]=1)[CH2:2][CH3:3].C1COCC1.O.[OH-].[Li+]>CO.O>[CH2:16]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]1[N:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[C:7]([CH3:15])[N:6]=1)[CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 21086142Methyl 2-(dipropylamino)-6-methylpyrimidine-4-carboxylate

Product 1

HCID 210854602-(Dipropylamino)-6-methylpyrimidine-4-carboxylic acidYield 82.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To methyl 2-(dipropylamino)-6-methylpyrimidine-4-carboxylate (0.450 g, 1.79 mmol) in MeOH (2 mL), water (1 mL), and THF (1 mL) was added lithium hydroxide monohydrate (0.113 g, 2.68 mmol). The mixture was stirred at room temperature for 1 h and then MeOH and THF were removed under reduced pressure. The pH of the residue was adjusted to approximately 5 and the resulting mixture was extracted with dichloromethane, dried over sodium sulfate, and concentrated to give 2-(dipropylamino)-6-methylpyrimidine-4-carboxylic acid (0.351 g) as a yellow solid.

Workup

  1. customMeOH and THF were removed under reduced pressure
  2. extractionthe resulting mixture was extracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cdc79e5202b84351980304bc5cd7a27a
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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