Ammonium Chloride → 4,5-Diamino-2-phenylpyrimidine

HRID 2213081Notes

Reaction equation

HRID 2213081 reaction equation
CC(C)([O-])C.[K+].Cl.CON.[C:11]1([C:17]2[N:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][N:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[NH4+:27]>CS(C)=O.[Cl-].[Zn+2].[Cl-]>[C:11]1([C:17]2[N:22]=[C:21]([NH2:27])[C:20]([NH2:23])=[CH:19][N:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 7552942-phenyl-5-nitropyrimidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 113680614,5-Diamino-2-phenylpyrimidineYield 80%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Zinc chloride (136 mg), potassium t-butoxide (505 mg) and O-methylhydroxylamine monohydrochloride (125 mg) were successively added to a solution of 2-phenyl-5-nitropyrimidine (201 mg, 1.00 mmol), which was prepared according to the method described in the Journal of American Chemical Society, 78, 1434–1437 (1956), in dimethyl sulfoxide (5 mL). The mixture was stirred at room temperature for 40 minutes, and saturated aqueous ammonium chloride was added thereto, then the mixture was extracted with ethyl acetate. The organic layer was washed with 5% aqueous sodium bicarbonate, dried over aqueous sodium sulfate, and concentrated in vacuo. The residue was dissolved in methanol (8 mL), and 10% palladium carbon (50 mg) was added thereto. The mixture was stirred at room temperature for one hour under a hydrogen atmosphere, and then filtered. The filtrate was concentrated in vacuo to give the title compound (148 mg, 80%) as a brown solid.

Workup

  1. customwas prepared
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with 5% aqueous sodium bicarbonate
  4. dry with materialdried over aqueous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in methanol (8 mL)
  7. addition10% palladium carbon (50 mg) was added
  8. stirringThe mixture was stirred at room temperature for one hour under a hydrogen atmosphere
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-583e3943fae04b9384a6955e3b299384
Source dataset
uspto-grants-2006_09
Patent number
US07105526B2

Reaction notes

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