HCID 69520520, compound → HCID 69521082, compound

HRID 1767745Notes

Reaction equation

HRID 1767745 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[N:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][N:8]=1)=[O:5]>C(O)C.C(OCC)(=O)C.[Pt]=O>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[N:8]=[CH:9][C:10]([NH2:13])=[CH:11][N:12]=1)=[O:5]

Participants

5

Reactant 1

HCID 69520520HCID 69520520, compound

Product 1

HCID 69521082HCID 69521082, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Platinum oxide (60 mg, 0.22 mmol) was added to a solution 2-(N-2-chlorobenzoyl)amino-5-nitropyrimidine (278 mg, 1.0 mmol) in ethanol (1 ml) and ethyl acetate (10 ml) at ambient temperature and the reaction stirred for 3 hours under an atmosphere of hydrogen. The reaction was filtered through a pad of celite and the solvents were evaporated in vacuo. Purification by flash chromatography on silica gel, eluting with 5% methanol in ethyl acetate yielded 2-(N-2-chlorobenzoyl)amino-5-aminopyrimidine (121 mg, 50% yield) as brown solid:

Workup

  1. filtrationThe reaction was filtered through a pad of celite
  2. customthe solvents were evaporated in vacuo
  3. customPurification by flash chromatography on silica gel
  4. washeluting with 5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-374bbd5ba3cc4a9fa80f30e1a3f7bd85
Source dataset
uspto-grants-2007_06
Patent number
US07235559B1

Reaction notes

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