Aniline → Pyrimido[5,4-d]pyrimidine

HRID 1867926Notes

Reaction equation

HRID 1867926 reaction equation
NC1C=CC=CC=1.Cl[C:9]1[N:10]=[C:11](Cl)[C:12]2[N:17]=[C:16](Cl)[N:15]=[C:14](Cl)[C:13]=2[N:20]=1>C(Cl)(Cl)Cl>[N:17]1[C:12]2[CH:11]=[N:10][CH:9]=[N:20][C:13]=2[CH:14]=[N:15][CH:16]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 97007Tetrachloropyrimido(5,4-d)pyrimidine

Product 1

HCID 21948654Pyrimido[5,4-d]pyrimidineYield 199.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

8.7 mL (95 mmol) of aniline may be slowly added dropwise to a solution of 4 g (19 mmol) of 2,4,6,8-tetrachloropyrimidopyrimidine in 50 mL of chloroform in a water bath at about 0° C. The results of the reaction may be verified by thin layer chromatography (TLC). The reaction mixture may be washed with an aqueous ammonium chloride solution and extracted with chloroform. The organic layer may be separated, distilled under reduced pressure to remove the solvent, and dried in an oven to yield approximately 5 g of Compound 5a. Compound 5a may be a substantially pale yellow solid.

Workup

  1. customThe results of the reaction
  2. washThe reaction mixture may be washed with an aqueous ammonium chloride solution
  3. extractionextracted with chloroform
  4. customThe organic layer may be separated
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customdried in an oven

Sources & evidence

ORD record
ord-80ecc067189e4267a4fab8d5cf886adf
Source dataset
uspto-grants-2009_12
Patent number
US07632947B2

Reaction notes

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