Lithium Hydroxide → 6-[(Cyclopropylmethyl)(propyl)amino]pyrimidine-4-carboxylic acid

HRID 1746661Notes

Reaction equation

HRID 1746661 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:16][CH2:17][CH3:18])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([O:14]C)=[O:13])[CH:7]=2)[CH2:3][CH2:2]1.[Li+].[OH-]>C1COCC1.CCO.O>[CH:1]1([CH2:4][N:5]([CH2:16][CH2:17][CH3:18])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([OH:14])=[O:13])[CH:7]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59447096HCID 59447096, compound

Product 1

HCID 594470006-[(Cyclopropylmethyl)(propyl)amino]pyrimidine-4-carboxylic acidYield 77.1%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

A solution of methyl 6-[(cyclopropylmethyl)(propyl)amino]pyrimidine-4-carboxylate (5.10 g; 20.5 mmol) in THF/EtOH/H2O (3/2/1, total volume 400 mL) was treated with an aqueous solution (1N) LiOH (60 mL; 60 mmol). The reaction mixture was stirred at room temperature for 1 h. The solvents were concentrated under vacuum and then water (200 mL) was added. The aqueous layer was washed with DCM then acidified to pH 5 by addition of 1N HCl solution (60 mL). The aqueous layer was extracted with DCM (3 times) and the combined organic layers were dried over MgSO4, filtered and concentrated under vacuum to give the title compound as a yellow solid (3.71 g, 77.1%).

Workup

  1. concentrationThe solvents were concentrated under vacuum
  2. additionwater (200 mL) was added
  3. washThe aqueous layer was washed with DCM
  4. additionthen acidified to pH 5 by addition of 1N HCl solution (60 mL)
  5. extractionThe aqueous layer was extracted with DCM (3 times)
  6. dry with materialthe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7e46631ce23d407bbbdf6c0da941a19f
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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