Thionyl Chloride → 4-Chloropyrido(3,4-d)pyrimidine

HRID 1784376Notes

Reaction equation

HRID 1784376 reaction equation
[N:1]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[C:4](O)=[N:3][CH:2]=1.S(Cl)([Cl:14])=O>CN(C)C=O>[Cl:14][C:4]1[C:5]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[N:1]=[CH:2][N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1785180321H-pyrido[3,4-d]pyrimidin-4-one

Product 1

HCID 122716344-Chloropyrido(3,4-d)pyrimidineYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of pyrido[3,4-d]pyrimidin-4-ol (33)(1.47 g, 10 mmol) in thionylchloride (30 ml) and dimethylformamide (50 μl, cat.) was heated to reflx (90° C.) for 1 hour. The mixture was then cooled and concentrated in vacuo and then diluted with CH2Cl2 (50 ml) which caused a suspension to form. The solid was removed by filtration, washed with cold CH2Cl2 (10 ml) to give the title compound (1.65 g, 99.4%) in sufficiently pure form to be used without any further purification. m/z (LC-MS, ESP): 166 [M+H]+, R/T=2.82 mins.

Workup

  1. temperaturewas heated
  2. custom(90° C.)
  3. customfor 1 hour
  4. temperatureThe mixture was then cooled
  5. concentrationconcentrated in vacuo
  6. additiondiluted with CH2Cl2 (50 ml) which
  7. customto form
  8. customThe solid was removed by filtration
  9. washwashed with cold CH2Cl2 (10 ml)

Sources & evidence

ORD record
ord-694e1296ac2d4f1a85bd1ff5e3a2b47a
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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