Methanol → 5-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]-2-methyl-nicotinic acid

HRID 2065570Notes

Reaction equation

HRID 2065570 reaction equation
C([O:3][C:4](=[O:27])[C:5]1[CH:10]=[C:9]([NH:11][C:12]2[N:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)=[CH:14][N:13]=2)[CH:8]=[N:7][C:6]=1[CH3:26])C.CO.O.[Li+].[OH-]>C1COCC1>[CH3:25][O:24][C:21]1[CH:20]=[CH:19][C:18]([C:15]2[CH:14]=[N:13][C:12]([NH:11][C:9]3[CH:8]=[N:7][C:6]([CH3:26])=[C:5]([CH:10]=3)[C:4]([OH:27])=[O:3])=[N:17][CH:16]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 673656505-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]-2-methyl-nicotinic acid ethyl ester

Product 1

HCID 581718975-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]-2-methyl-nicotinic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of the 5-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-2-methyl-nicotinic acid ethyl ester 9 (0.9 mmol) in THF:MeOH:H2O=3:2:1 (7 mL), is added 6M LiOH (2.7 mmol). The reaction mixture is stirred at rt for 12 h. After this time the solvent is removed under vacuum, the residue is diluted with H2O (6 mL) and the pH neutralized with 6M HCl. The solid formed is filtered, washed with water and dried in a vacuum oven for 12 h to afford 5-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-2-methyl-nicotinic acid 10 as off white solid, which is used in the next step without further purification. MS (m/z) (M+1)+: 337.2.

Workup

  1. customAfter this time the solvent is removed under vacuum
  2. additionthe residue is diluted with H2O (6 mL)
  3. customThe solid formed
  4. filtrationis filtered
  5. washwashed with water
  6. customdried in a vacuum oven for 12 h

Sources & evidence

ORD record
ord-840e7059b585488e83fba86fc725db6d
Source dataset
uspto-grants-2012_10
Patent number
US08288540B2

Reaction notes

Loading…