Dimethylformamide → 4,6-Dichloropyrido[3,4-d]pyrimidine

HRID 1264066Notes

Reaction equation

HRID 1264066 reaction equation
CN(C=O)C.[Cl:6][C:7]1[N:17]=[CH:16][C:10]2[N:11]=[CH:12][NH:13][C:14](=O)[C:9]=2[CH:8]=1.S(Cl)([Cl:20])=O>C1(C)C=CC=CC=1>[Cl:20][C:14]1[C:9]2[CH:8]=[C:7]([Cl:6])[N:17]=[CH:16][C:10]=2[N:11]=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1354805256-chloro-3H,4H-pyrido[3,4-d]pyrimidin-4-one

Product 1

HCID 108218764,6-Dichloropyrido[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

DMF (0.1 ml) was added to 6-chloro-3H-pyrido[3,4-d]pyrimidin-4-one (1.82 g, 10 mmol) followed by dropwise addition of thionyl chloride (10 ml). The flask was fitted with a condenser and a drying tube and the contents heated to reflux for 20 minutes whereupon the solids dissolved. The heating was continued for a further 1 h and then cooled. Toluene was added to wash the sides of the flask and the solvents were evaporated in vacuo. Azeotroping with toluene was repeated twice and the crude so obtained was taken through to the next step.

Workup

  1. customThe flask was fitted with a condenser and a drying tube
  2. temperaturethe contents heated
  3. temperatureto reflux for 20 minutes whereupon the solids
  4. dissolutiondissolved
  5. temperaturecooled
  6. washto wash the sides of the flask
  7. customthe solvents were evaporated in vacuo
  8. customAzeotroping with toluene
  9. customthe crude so obtained

Sources & evidence

ORD record
ord-9e53ee6340ac4313a395d2a710f50071
Source dataset
uspto-grants-2003_04
Patent number
US06541481B2

Reaction notes

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