HCID 13277355, compound → HCID 13277359, compound

HRID 904890Notes

Reaction equation

HRID 904890 reaction equation
[CH:1]([N:4]([CH:20]([CH3:22])[CH3:21])[CH2:5][CH2:6][N:7]1[C:12]2[N:13]=[C:14]([CH3:18])[CH:15]=[C:16]([CH3:17])[C:11]=2[CH2:10][NH:9][C:8]1=[O:19])([CH3:3])[CH3:2]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:20]([N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6][N:7]1[C:12]2[N:13]=[C:14]([CH3:18])[CH:15]=[C:16]([CH3:17])[C:11]=2[CH:10]=[N:9][C:8]1=[O:19])([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 13277355HCID 13277355, compound

Product 1

HCID 13277359HCID 13277359, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(2-diisopropylaminoethyl)-5,7-dimethyl-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-2-one (3.5 g, 11.1 mmol) in methylene chloride (100 ml) containing activated manganese dioxide (9.0 g) is heated at reflux for 16 hours. The solution is filtered hot to remove the manganese dioxide and the manganese dioxide is extracted twice with hot chloroform. The organic extracts are combined, dried and evaporated to give 3.6 g of crude product which is crystallized from cyclohexane to give 2.0 g of pure title product; m.p.: 148°-150° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 16 hours
  3. filtrationThe solution is filtered hot
  4. customto remove the manganese dioxide
  5. extractionthe manganese dioxide is extracted twice with hot chloroform
  6. customdried
  7. customevaporated
  8. customto give 3.6 g of crude product which
  9. customis crystallized from cyclohexane

Sources & evidence

ORD record
ord-1658120013a2498d8157574f6dad7ee3
Source dataset
uspto-grants-1983_12
Patent number
US04420615

Reaction notes

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