Hydrochloric Acid → 5-[2-(Pyridin-3-ylamino)-pyrimidin-4-yl]-thiophene-2-carboxylic acid

HRID 1012186Notes

Reaction equation

HRID 1012186 reaction equation
C([O:3][C:4]([C:6]1[S:7][C:8]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[N:12]=2)=[CH:9][CH:10]=1)=[O:5])C.[Li+].[OH-].Cl>CO.O>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([NH:17][C:13]2[N:12]=[C:11]([C:8]3[S:7][C:6]([C:4]([OH:5])=[O:3])=[CH:10][CH:9]=3)[CH:16]=[CH:15][N:14]=2)[CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 594686225-[2-(Pyridin-3-ylamino)-pyrimidin-4-yl]-thiophene-2-carboxylic acid ethyl ester

Product 1

HCID 594686335-[2-(Pyridin-3-ylamino)-pyrimidin-4-yl]-thiophene-2-carboxylic acidYield 72.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

5-[2-(Pyridin-3-ylamino)-pyrimidin-4-yl]-thiophene-2-carboxylic acid ethyl ester (76 mg, 0.209 mmol) was saponified by treatment with 4 N LiOH (0.524 mL, 2.09 mmol) in MeOH (1.5 mL) at 40° C. for 15 h. 6 N HCl (2.09 mmol) was added and the mixture was diluted with water. The precipitate was collected by filtration, rinsed with EtOH and dried on vacuum to afford title compound (45 mg, 72%). The crude material was used in the next step.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washrinsed with EtOH
  3. customdried on vacuum

Sources & evidence

ORD record
ord-f9e6582d26984fa8859f9ec13fb20300
Source dataset
uspto-grants-2011_07
Patent number
US07977481B2

Reaction notes

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