Thionyl Chloride → 6-(Benzyloxy)-4-chloropyrido[3,4-d]pyrimidine

HRID 566390Notes

Reaction equation

HRID 566390 reaction equation
[CH2:1]([O:8][C:9]1[N:19]=[CH:18][C:12]2[N:13]=[CH:14][N:15]=[C:16](O)[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:22])=O>CN(C=O)C>[CH2:1]([O:8][C:9]1[N:19]=[CH:18][C:12]2[N:13]=[CH:14][N:15]=[C:16]([Cl:22])[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1785180356-phenylmethoxy-1H-pyrido[3,4-d]pyrimidin-4-one

Product 1

HCID 227274286-(Benzyloxy)-4-chloropyrido[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

6-Benzyloxy-4-hydroxy-pyrido[3,4-d]pyrimidine (1.033 g, 4.1 mmol) was suspended in thionyl chloride (10 ml) under a nitogen atmosphere. DMF (3 drops) was added and the mixture was heated to reflux with stirring for 5.5 hours to give a dark solution, and then left to stand under nitrogen overnight. The mixture was concentrated in vacuo, azeotroping twice with toluene to remove all traces of thionyl cloride and acidic by-products. The material was further dried for two hours in vacuo to give the title compound as a brown solid, used without further purification; δH [2H6]DMSO 8.77(1H,s), 8.13(1H,s), 7.30-7.52 (6H,m), 5.45 (2H,s).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. customto give a dark solution
  4. waitleft
  5. waitto stand under nitrogen overnight
  6. concentrationThe mixture was concentrated in vacuo
  7. customazeotroping twice with toluene
  8. customto remove all traces of thionyl cloride and acidic by-products
  9. customThe material was further dried for two hours in vacuo

Sources & evidence

ORD record
ord-3a7f5c11d6434fa980d7d4140415ba86
Source dataset
uspto-grants-2001_01
Patent number
US06174889B1

Reaction notes

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