5-Nitropyrimidin-2-amine → HCID 69521039, compound

HRID 1767740Notes

Reaction equation

HRID 1767740 reaction equation
[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:9][C:10]1[N:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][N:11]=1>N1C=CC=CC=1.Cl>[CH:1]1([C:6]([NH:9][C:10]2[N:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][N:11]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 764905-Nitropyrimidin-2-amineHCID 78284Cyclopentanecarbonyl chloride

Product 1

HCID 69521039HCID 69521039, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Procedure

Cyclopentanoyl chloride (946 mg, 7.14 mmol) was added dropwise to a stirred suspension of 2-amino-5-nitropyrimidine (1.0 g, 7.14 mmol) in pyridine (10 ml) and the reaction was heated at reflux for 4 hours under an inert atmosphere. The reaction mixture was cooled then stirred in 2N hydrochloric acid (100 ml) and the resulting solid collected by suction filtration. Purification by flash chromatography on silica gel, eluting with 2% methanol in dichloromethane, yielded 2-(N-cyclopentanoyl)amino-5-nitropyrimidine (812 mg, 48% yield) as an beige solid:

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 4 hours under an inert atmosphere
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe resulting solid collected by suction filtration
  5. customPurification by flash chromatography on silica gel
  6. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-367986237d1b40d69431518c0e38f823
Source dataset
uspto-grants-2007_06
Patent number
US07235559B1

Reaction notes

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