Aniline → Pyrimido[5,4-d]pyrimidine

HRID 2238693Notes

Reaction equation

HRID 2238693 reaction equation
Cl[C:2]1[N:3]=[C:4](Cl)[C:5]2[N:10]=[C:9](Cl)[N:8]=[C:7](Cl)[C:6]=2[N:13]=1.NC1C=CC=CC=1>C(Cl)(Cl)Cl>[N:10]1[C:5]2[CH:4]=[N:3][CH:2]=[N:13][C:6]=2[CH:7]=[N:8][CH:9]=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

In accord with the synthesis illustrated above, 4 g (19 mmol) of 2,4,6,8-tetrachloropyrimidopyrimidine was added to 50 ml of chloroform, and 8.7 ml (95 mmol) of aniline was slowly added in droplets thereto in a bath at 0° C. After the completion of the reaction was confirmed through TLC, the resulting reaction solution was washed with an aqueous ammonium chloride solution and then extracted with chloroform to separate an organic layer. Thereafter, the organic layer was distilled under reduced pressure to remove the solvent and then dried in an oven, yielding 5 g of a pale yellow solid 5a NMR analysis of the pale yellow solid produced the following data: 1H-NMR (DMSO-d6) d(ppm) 7.23 (t, 2H, J=7.3 z), 7.46 (t, 41, J=7.8 Hz), 7.87 (t, 4H, J=8.1 Hz), 8.66 (s, 2H).

Workup

  1. additionwas slowly added in droplets
  2. customat 0° C
  3. customthe resulting reaction solution
  4. washwas washed with an aqueous ammonium chloride solution
  5. extractionextracted with chloroform
  6. customto separate an organic layer
  7. distillationThereafter, the organic layer was distilled under reduced pressure
  8. customto remove the solvent
  9. customdried in an oven

Sources & evidence

ORD record
ord-74c788c7f7894681b37456a3c06774c7
Source dataset
uspto-grants-2010_05
Patent number
US07719000B2

Reaction notes

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