Triethylamine → tert-Butyl (2-oxo-3-pyrimidin-4-yl-2,3-dihydro-1H-benzimidazol-1-yl)acetate

HRID 1675751Notes

Reaction equation

HRID 1675751 reaction equation
[C:1]([O:5][C:6](=[O:25])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([C:17]2[CH:22]=[C:21](Cl)[N:20]=[CH:19][N:18]=2)[C:9]1=[O:24])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>CCO.[Pd]>[O:24]=[C:9]1[N:8]([CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:25])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]1[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][N:18]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86607781tert-Butyl [3-(6-chloropyrimidin-4-yl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate

Product 1

HCID 86607782tert-Butyl (2-oxo-3-pyrimidin-4-yl-2,3-dihydro-1H-benzimidazol-1-yl)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl[3-(6-chloropyrimidin-4-yl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate from Step A (260 mg, 0.720 mmol), 10% Pd/C (23 mg) and triethylamine (0.150 mL, 1.08 mmol) in EtOH (5 mL) was stirred under an atmosphere of hydrogen (ca. 1 atm) for 2 h. The mixture was filtered through a pad of Celite, washing with EtOH, and the filtrate was concentrated to give the title compound. MS: m/z=327 (M+1).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washwashing with EtOH
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a6754c131c6f409bb7b991b59fcd3016
Source dataset
uspto-grants-2011_08
Patent number
US08003792B2

Reaction notes

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