2,5-Hexanedione → 2-[(S)-1-phenylethylamino]-4-[5-(2,5-dimethylpyrrol-1-yl)benzimidazol-1-yl]pyrimidine

HRID 2300883Notes

Reaction equation

HRID 2300883 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([NH2:25])=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:26]([CH2:30][C:31](=O)[CH3:32])[C:27]([CH3:29])=O>C(O)(=O)C.C1C=CC=CC=1.C([O-])(O)=O.[Na+]>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([N:25]5[C:31]([CH3:32])=[CH:30][CH:26]=[C:27]5[CH3:29])=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 80352,5-HexanedioneHCID 98839772-[(S)-1-phenylethylamino]-4-[5-aminobenzimidazol-1-yl]pyrimidine

Product 1

HCID 599247742-[(S)-1-phenylethylamino]-4-[5-(2,5-dimethylpyrrol-1-yl)benzimidazol-1-yl]pyrimidine

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 241BenzeneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-[(S)-1-Phenylethylamino]-4-[5-aminobenzimidazol-1-yl]pyrimidine (EXAMPLE 79) (100 mg) and acetonyl acetone(0.04 mL)and acetic acid (20 drops) were dissolved in benzene (10 mL) and refluxed with Dean-Stark apparatus for 2 hours. After cooling to room temperature, the solution was then diluted with 10 mL of aqueous saturated NaHCO3 and extracted with 2×10 mL of of EtOAc. The combined organic extracts were then dried (MgSO4) and concentrated under reduced pressure. The residue was purified with preparatory thin-layer chromatography (SiO2, 5% MeOH in CH2Cl2) to yield 17 mg of the title compound. Mass spectrum (ESI) 408.1 (M+).

Workup

  1. temperaturerefluxed with Dean-Stark apparatus for 2 hours
  2. extractionextracted with 2×10 mL of of EtOAc
  3. dry with materialThe combined organic extracts were then dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with preparatory thin-layer chromatography (SiO2, 5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-97d23dfa6cee4206b382835f4925bc45
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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