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

HRID 1921174Notes

Reaction equation

HRID 1921174 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:9]2=[O:25])[CH:3]=1.C(N(CC)CC)C>CCO.[Pd]>[O:25]=[C:9]1[N:10]([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]1[C:4]1[CH:3]=[CH:2][N:7]=[CH:6][N:5]=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-8ee055d0125b406182bc852a2ef0f0c4
Source dataset
uspto-grants-2012_05
Patent number
US08173655B2

Reaction notes

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