Lithium Hydroxide → 5-((5-Chloro-4-(methylamino)pyrimidin-2-yl)amino)-1-methyl-1H-pyrazole-3-carboxylic acid

HRID 2409101Notes

Reaction equation

HRID 2409101 reaction equation
[Cl:1][C:2]1[C:3]([NH:19][CH3:20])=[N:4][C:5]([NH:8][C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15]([O:17]C)=[O:16])[CH:10]=2)=[N:6][CH:7]=1.[Li+].[OH-].O1CCCC1>O>[Cl:1][C:2]1[C:3]([NH:19][CH3:20])=[N:4][C:5]([NH:8][C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 69081130methyl 5-(5-chloro-4-(methylamino)pyrimidin-2-ylamino)-1-methyl-1H-pyrazole-3-carboxylate

Product 1

HCID 690837945-((5-Chloro-4-(methylamino)pyrimidin-2-yl)amino)-1-methyl-1H-pyrazole-3-carboxylic acidYield 63.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100 mL round bottom flask equipped with a stir bar was added 0.964 g of methyl 5-(5-chloro-4-(methylamino)pyrimidin-2-ylamino)-1-methyl-1H-pyrazole-3-carboxylate, 0.28 g of LiOH, 15 mL of tetrahydrofuran and 10 mL of water. The reaction was stirred at room temperature for 18 hours. The tetrahydrofuran was removed in vacuo and the aqueous layer was acidified to pH 5 with 1N HCl. The aqueous layer was partitioned with ethyl acetate and the organic layer washed with brine, dried over MgSO4, filtered and concentrated to give 0.58 g of 5-(5-chloro-4-(methylamino)pyrimidin-2-ylamino)-1-methyl-1H-pyrazole-3-carboxylic acid which was used without further purification.

Workup

  1. customTo a 100 mL round bottom flask equipped with a stir bar
  2. customThe tetrahydrofuran was removed in vacuo
  3. customThe aqueous layer was partitioned with ethyl acetate
  4. washthe organic layer washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-90e89002ac334f2b9e04456e77a3253e
Source dataset
uspto-grants-2014_08
Patent number
US08815882B2

Reaction notes

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