Hydrochloric Acid → 6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid

HRID 1260300Notes

Reaction equation

HRID 1260300 reaction equation
C([O:3][C:4]([C:6]1[C:11]([NH:12][C:13]2[CH:14]=[N:15][CH:16]=[N:17][CH:18]=2)=[CH:10][CH:9]=[C:8]([CH:19]2[CH2:21][CH2:20]2)[N:7]=1)=[O:5])C.[OH-].[Na+].Cl>CCO>[CH:19]1([C:8]2[N:7]=[C:6]([C:4]([OH:5])=[O:3])[C:11]([NH:12][C:13]3[CH:18]=[N:17][CH:16]=[N:15][CH:14]=3)=[CH:10][CH:9]=2)[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 583680566-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 583680496-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acidYield 77.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 6-cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid ethyl ester (1.85 g, 6.5 mmol) from example A-2 in EtOH (15 ml) was treated with 1N NaOH (13 ml). The reaction mixture was stirred at r.t. overnight. The compact suspension was brought to pH 6 by addition of 1N HCl. The solid was collected by filtration, washed with EtOH and dried to give the product (1.29 g, 77%) as off-white solid.

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with EtOH
  3. customdried

Sources & evidence

ORD record
ord-757b4f3a300b4375830f78a71a480946
Source dataset
uspto-grants-2013_06
Patent number
US08470820B2

Reaction notes

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