Thionyl Chloride → HCID 58628200, compound

HRID 2113624Notes

Reaction equation

HRID 2113624 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](O)[C:9]2[CH:15]=[CH:14][C:13]([C:16]3[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][N:17]=3)=[N:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].S(Cl)([Cl:26])=O>>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Cl:26])[C:9]2[CH:15]=[CH:14][C:13]([C:16]3[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][N:17]=3)=[N:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 178470307HCID 178470307, compound

Product 1

HCID 58628200HCID 58628200, compound

Procedure

Dissolve 4-hydroxy-7-(3-methyl-pyridin-2-yl)-pyrido[2,3-d]pyrimidine-2-carboxylic acid ethyl ester (345 mg, 1.11 mmol) in thionyl chloride (15 mL) and heat the mixture at reflux overnight. Cool the mixture to room temperature and remove the excess thionyl chloride in vacuo. Dissolve the crude reaction mixture in CH2Cl2 (50 mL) and wash with saturated NaHCO3 (aq). Dry the organic layer over Na2SO4 and remove the solvent under reduced pressure to yield the title compound. MS 329.12 (M+1)

Workup

  1. temperatureheat the mixture
  2. temperatureat reflux overnight
  3. customremove the excess thionyl chloride in vacuo
  4. dissolutionDissolve the crude
  5. customreaction mixture in CH2Cl2 (50 mL)
  6. washwash with saturated NaHCO3 (aq)
  7. dry with materialDry the organic layer over Na2SO4
  8. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-c042244a4e6c4f98bf4782c0982e778a
Source dataset
uspto-grants-2008_10
Patent number
US07432275B2

Reaction notes

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