2-[(S)-1-phenylethylamino]-4-[5-aminobenzimidazol-1-yl]pyrimidine → 2-[(S)-1-phenylethylamino]-4-[5-(pyrimidin-4-yl)aminobenzimidazol-1-yl]pyrimidine

HRID 2300894Notes

Reaction equation

HRID 2300894 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.[H][H]>CO.[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][C:23]([NH:25][C:12]5[CH:13]=[CH:14][N:15]=[CH:10][N:11]=5)=[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

5

Reactant 2

HCID 98839772-[(S)-1-phenylethylamino]-4-[5-aminobenzimidazol-1-yl]pyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 99093772-[(S)-1-phenylethylamino]-4-[5-(pyrimidin-4-yl)aminobenzimidazol-1-yl]pyrimidineYield 63.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-[(S)-1-phenylethylamino]-4-[5-aminobenzimidazol-1-yl]pyrimidine (14.0 mg) was dissolved in 2 mL MeOH, 10%Pd/C (20.3 mg) added, the system fitted with a balloon of hydrogen, purging the system twice and leaving the reaction stirring at room temperature for 23 h. The mixture was then filtered through Celite®, washing thoroughly with methanol, and the solvent removed in vacuo. The residue was purified on silica gel (2-5%(2M NH3 in MeOH)/CH2Cl2) to yield 5.5 mg of the title compound. Mass spectrum (ESI) 409.4 (M+1).

Workup

  1. custompurging the system twice
  2. customleaving the reaction
  3. filtrationThe mixture was then filtered through Celite®
  4. washwashing thoroughly with methanol
  5. customthe solvent removed in vacuo
  6. customThe residue was purified on silica gel (2-5%(2M NH3 in MeOH)/CH2Cl2)

Sources & evidence

ORD record
ord-ec468ceaac1e48b9923c33120aaac479
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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