Thionyl Chloride → 5-Chloro-5-(4,6-dimethoxy-2-pyrimidinyl)furo[3,4-b]pyridin-7(5H)-one

HRID 863762Notes

Reaction equation

HRID 863762 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]([C:13]2[C:14]([C:19]([OH:21])=[O:20])=[N:15][CH:16]=[CH:17][CH:18]=2)=O)[N:4]=1.S(Cl)([Cl:24])=O>C(Cl)(Cl)(Cl)Cl>[Cl:24][C:11]1([C:5]2[N:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[N:4]=2)[C:13]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[C:19](=[O:20])[O:21]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15300825HCID 15300825, compound

Product 1

HCID 190506415-Chloro-5-(4,6-dimethoxy-2-pyrimidinyl)furo[3,4-b]pyridin-7(5H)-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
70 °C

Procedure

45.53 g of 3-[(4,6-dimethoxy-2-pyrimidinyl)carbonyl]-2-pyridinecarboxylic acid are suspended in 700 ml of carbon tetrachloride and 186.4 g of thionyl chloride added with stirring. The suspension is heated to 70° C. for 4 hrs and the reaction mixture then cooled to RT and the excess thionyl chloride and carbon tetrachloride evaporated off to give the title compound as a tan solid m.p. 146°-148° C.

Workup

  1. temperaturethe reaction mixture then cooled to RT
  2. customthe excess thionyl chloride and carbon tetrachloride evaporated off

Sources & evidence

ORD record
ord-6323326f8c8d463085a4014cdd0b22a7
Source dataset
uspto-grants-1996_10
Patent number
US05561101

Reaction notes

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