HCID 86758760, compound → HCID 59924788, compound

HRID 2300845Notes

Reaction equation

HRID 2300845 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][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[C:12]([N:25]=[N+]=[N-])[N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.[Pd]>[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][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[C:12]([NH2:25])[N:11]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 86758760HCID 86758760, compound

Product 1

HCID 59924788HCID 59924788, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of of 2-[(S)-1-phenylethylamino]-4-[benzimidazol-1-yl]-6-azidopyrimidine (11 mg, 0.03 mmol) in ethanol (1 mL) was added 10% palladium on carbon (11 mg), then the mixture was charged with H2 via balloon. The reaction mixture was stirred for 2 h, then filtered over packed Celite and rinsed thoroughly with EtOAc. The solvent was concentrated under reduced pressure, and the crude material was purified by preparative thin layer chromatography eluting with 3% MeOH/CH2Cl2 to afford 6.2 mg of the title compound. Mass spectrum 331.2 (CI, M+1).

Workup

  1. additionthe mixture was charged with H2 via balloon
  2. filtrationfiltered
  3. washrinsed thoroughly with EtOAc
  4. concentrationThe solvent was concentrated under reduced pressure
  5. customthe crude material was purified by preparative thin layer chromatography
  6. washeluting with 3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-04dd47f9d3e94d989e811970f90334d1
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

Loading…