Methanol → HCID 15239968, compound

HRID 1653632Notes

Reaction equation

HRID 1653632 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[C:13]([C:23]([O:25]C)=[O:24])=[N:14][C:15]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:16][CH:17]=2)[N:4]=1.[OH-].[K+].CO.COCCOC>O>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([O:11][C:12]2[C:13]([C:23]([OH:25])=[O:24])=[N:14][C:15]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:16][CH:17]=2)[N:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 80711,2-DimethoxyethaneHCID 14797Potassium HydroxideHCID 15239965HCID 15239965, compound

Product 1

HCID 15239968HCID 15239968, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.44 g (4 mmol) of methyl 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-(1-pyrrolidinyl)picolinate and 0.67 g (12 mmol) of potassium hydroxide were added to 30 ml of methanol, 30 ml of 1,2-dimethoxyethane and 10 ml of water, and the mixture was reacted at 40° C. for 4 hours. The solvent was distilled off, and water was added to the residue. The mixture was acidified (pH=4) by 10% hydrochloric acid, then extracted with chloroform and ethyl acetate, dried and concentrated, and then crystallized from diisopropyl ether to obtain the desired product.

Workup

  1. customthe mixture was reacted at 40° C. for 4 hours
  2. distillationThe solvent was distilled off
  3. additionwater was added to the residue
  4. extractionextracted with chloroform and ethyl acetate
  5. customdried
  6. concentrationconcentrated
  7. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-c15917f6d8b646fc9fc307d2cf5f1b96
Source dataset
uspto-grants-1995_04
Patent number
US05403816

Reaction notes

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