Hydrochloric Acid → 4-(4-(1H-1,2,4-triazol-1-yl)phenylamino)-2-chloropyrimidine-5-carboxylic acid

HRID 1880285Notes

Reaction equation

HRID 1880285 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]3[C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][N:16]=[C:15]([Cl:24])[N:14]=3)=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.[Li+].[OH-].Cl>C1COCC1>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([NH:12][C:13]3[C:18]([C:19]([OH:21])=[O:20])=[CH:17][N:16]=[C:15]([Cl:24])[N:14]=3)=[CH:10][CH:11]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57471895Ethyl 4-(4-(1H-1,2,4-triazol-1-yl)phenylamino)-2-chloropyrimidine-5-carboxylate

Product 1

HCID 574718944-(4-(1H-1,2,4-triazol-1-yl)phenylamino)-2-chloropyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Ethyl 4-(4-(1H-1,2,4-triazol-1-yl)phenylamino)-2-chloropyrimidine-5-carboxylate (ii) (870 mg, 2.523 mmol), in THF (12 mL), was added 1M LiOH (3.30 mL, 3.30 mmol, 1.30 equiv), and the mixture was stirred at room temperature for 3 h. Then THF was rotavopped off, and the aqueous mixture was acidified with 2N HCl to pH 2. The precipitated solid product was collected by filtration, rinsed with water, and air dried; yield 712 mg (89%).

Workup

  1. filtrationThe precipitated solid product was collected by filtration
  2. washrinsed with water, and air
  3. customdried

Sources & evidence

ORD record
ord-50716f206c9944b7a100a48ab4ad9330
Source dataset
uspto-grants-2012_11
Patent number
US08318755B2

Reaction notes

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