4,5-Diaminopyrimidine → HCID 178424861, compound

HRID 1858099Notes

Reaction equation

HRID 1858099 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([N:27]=[C:28]=S)[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:40][C:41]1[C:46]([NH2:47])=[CH:45][N:44]=[CH:43][N:42]=1>[Hg]=O>[NH3:8].[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([NH:27][C:28]3[NH:40][C:41]4[C:46]([N:47]=3)=[CH:45][N:44]=[CH:43][N:42]=4)[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 837034,5-DiaminopyrimidineHCID 54130839HCID 54130839, compound

Product 2

HCID 222AmmoniaHCID 178424861HCID 178424861, compoundYield 8.4%

Reagents, catalysts & solvents 1

HCID 30856Mercuric oxideCatalyst

Procedure

To a solution of 2-{2-[7-chloro-3-(3,5-dimethylphenyl)-6-isothiocyanato-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (210 mg in 5 mL toluene) was added 250 mg mercury(II) oxide followed by 130 mg 4,5-diaminopyrimidine and the mixture heated to reflux on an oil bath. After 48 hours, the mixture was cooled to room temperature and the reaction quenched by the addition of 2N hydrochloric acid (4 mL). The solvents were removed in vacuo and the residue treated with 2N ammonia in methanol (10 mL) then concentrated once again. The residue was washed with chloroform and the solids removed by filtration. Concentration of the organics and purification by flash chromatography on silica gel (ethyl acetate:hexane, 1:1; then chloroform:2N ammonia in methanol, 9:1) gave the title compound (10 mg).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux on an oil bath
  3. customthe reaction quenched by the addition of 2N hydrochloric acid (4 mL)
  4. customThe solvents were removed in vacuo
  5. additionthe residue treated with 2N ammonia in methanol (10 mL)
  6. concentrationthen concentrated once again
  7. washThe residue was washed with chloroform
  8. customthe solids removed by filtration
  9. customConcentration of the organics and purification by flash chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-deb8ecf52c49440390ddc8b4797da974
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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