Sodium hydride → HCID 59924884, compound

HRID 2300884Notes

Reaction equation

HRID 2300884 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]([OH: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-].[Na+].[CH2:28]([O:35][C:36]([N:38]1[CH2:42][CH2:41][CH2:40][CH:39]1[CH2:43]OS(C)(=O)=O)=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C.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]([O:25][CH2:43][CH:39]5[CH2:40][CH2:41][CH2:42][N:38]5[C:36]([O:35][CH2:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[O:37])=[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 3

HCID 24758Sodium hydrideHCID 18375727HCID 18375727, compoundHCID 59924895HCID 59924895, compound

Product 1

HCID 59924884HCID 59924884, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

2-[(S)-1-Phenylethylamino]-4-[5-hydroxybenzimidazol-1-yl]-pyrimidine (25 mg) was dissolved in DMF (2.0 mL) and NaH (60%, 6.0 mg) was added followed by N-benzyloxycarbonyl-2-(methanesulfonyloxy)methylpyrrolidine (20 mg) and the resulting suspension was heated to 80° C. for 1 hour. 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 preparative thin-layer chromatography (SiO2, 5% MeOH in CH2Cl2) to yield 17 mg of 2-[(S)-1-Phenylethylamino]-4-[5-((N-benzyloxycarbonyl-pyrrolidin-2-yl)methoxy)benzimidazol-1-yl]pyrimidine. Mass spectrum (ESI) 549.3 (M+1).

Workup

  1. temperatureAfter cooling to room temperature
  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 preparative thin-layer chromatography (SiO2, 5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-02de94712e694780a6b6b67e94a82f7b
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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