3-(3-tert-butoxycarbonylaminopropyl)-1-benzyl-5-bromo-1H-pyrimidine-2,4-dione → 3-(3-tert-butoxycarbonylaminopropyl)-1-benzyl-5-phenyl-1H-pyrimidine-2,4-dione

HRID 1977236Notes

Reaction equation

HRID 1977236 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([O:12][C:13]([NH:15][CH2:16][CH2:17][CH2:18][N:19]1[C:24](=[O:25])[C:23](Br)=[CH:22][N:21]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:20]1=[O:34])=[O:14])([CH3:11])([CH3:10])[CH3:9]>[Cl-].[Zn+2].[Cl-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)(O)[O-].[Na+]>[C:8]([O:12][C:13]([NH:15][CH2:16][CH2:17][CH2:18][N:19]1[C:24](=[O:25])[C:23]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:22][N:21]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:20]1=[O:34])=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 2

HCID 155501603-(3-tert-butoxycarbonylaminopropyl)-1-benzyl-5-bromo-1H-pyrimidine-2,4-dioneHCID 178506676HCID 178506676, compound

Product 1

HCID 155501613-(3-tert-butoxycarbonylaminopropyl)-1-benzyl-5-phenyl-1H-pyrimidine-2,4-dione

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of zinc chloride (0.5 M in tetrahydrofuran, 2.3 mL, 1.1 mL) and a solution of phenyllithium (1.8 M in tetrahydrofuran, 3.2 mL, 5.7 mmol) were stirred together at −78° C. under inert atmosphere for 10 min when the reaction was warmed to ambient temperature. Tetrakis(triphenylphosphine)palladium(0) (66 mg, 0.057 mmol) and 3-(3-tert-butoxycarbonylaminopropyl)-1-benzyl-5-bromo-1H-pyrimidine-2,4-dione (500 mg, 1.1 mmol) were added and the reaction stirred at ambient temperature 20 h. The reaction mixture was treated with saturated sodium bicarbonate (50 mL) and extracted into ethyl acetate (3×50 mL). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting mixture was purified by pressurized silica gel chromatography (25-35% ethyl acetate in hexane) to provide 3-(3-tert-butoxycarbonylaminopropyl)-1-benzyl-5-phenyl-1H-pyrimidine-2,4-dione.

Workup

  1. extractionextracted into ethyl acetate (3×50 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting mixture was purified by pressurized silica gel chromatography (25-35% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8b4f2ac19a2a4f549a760d654f898714
Source dataset
uspto-grants-2001_05
Patent number
US06232318B1

Reaction notes

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