Methanol → 5-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]-pyridine-2-carboxylic acid

HRID 2065567Notes

Reaction equation

HRID 2065567 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([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:7][N:6]=1)=[O:4].CO.O.[Li+].[OH-]>C1COCC1>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([C:15]2[CH:14]=[N:13][C:12]([NH:11][C:8]3[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=3)=[N:17][CH:16]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 673658245-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 581718455-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]-pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]pyridine-2-carboxylic acid methyl ester 4 (0.3 mmol) in THF:MeOH:H2O=3:2:1 (5 mL), is added 6M LiOH (1.8 mmol). The reaction mixture is stirred at it 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 that precipitates out is collected, washed with water and dried in a vacuum oven for 12 h to afford 5-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-pyridine-2-carboxylic acid 5 as a yellow solid, which is used in the next step without further purification. MS (m/z) (M+1)+: 323.2.

Workup

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

Sources & evidence

ORD record
ord-2ec2a6d84e524ac89e4be6d6f14adedf
Source dataset
uspto-grants-2012_10
Patent number
US08288540B2

Reaction notes

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