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

HRID 1977235Notes

Reaction equation

HRID 1977235 reaction equation
[CH2:1]([N:8]1[CH:13]=[C:12]([Br:14])[C:11](=[O:15])[NH:10][C:9]1=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[C:19]([O:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29]Br)=[O:25])([CH3:22])([CH3:21])[CH3:20]>CN(C)C=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:19]([O:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][N:10]1[C:11](=[O:15])[C:12]([Br:14])=[CH:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]1=[O:16])=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 52766591-Benzyl-5-bromo-1,2,3,4-tetrahydropyrimidine-2,4-dione

Product 1

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

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-benzyl-5-bromo-1H-pyrimidine-2,4-dione (1.0 g, 3.6 mmol) in N,N-dimethylformamide (15 mL) was added tetrabutylammonium bromide (46 mg, 0.14 mmol) and sodium hydroxide (160 mg, 3.9 mmol). The suspension was stirred vigorously, heated to 60° C. for 1.5 h and then cooled to ambient temperature. N-tert-butoxycarbonyl-3-bromopropylamine (0.93 g, 3.9 mmol) was added, the reaction was heated to 50° C. for 20 h and then concentrated in vacuo. The residue was taken up in ethyl acetate:water (1:1 100 mL), the layers separated and the aqueous layer extracted with ethyl acetate (3×50 mL). The organic layers were combined and washed with 0.5 M sodium hydroxide (1×50 mL), water (1×50 mL), brine (1×100 mL), dried with magnesium sulfate, filtered and concentrated in vacuo. The resulting oil was purified by pressurized silica gel chromatography (40% ethyl acetate in hexane) to provide 3-(3-tert-butoxycarbonylaminopropyl)-1-benzyl-5-bromo-1H-pyrimidine-2,4-dione.

Workup

  1. temperaturecooled to ambient temperature
  2. temperaturethe reaction was heated to 50° C. for 20 h
  3. concentrationconcentrated in vacuo
  4. customthe layers separated
  5. extractionthe aqueous layer extracted with ethyl acetate (3×50 mL)
  6. washwashed with 0.5 M sodium hydroxide (1×50 mL), water (1×50 mL), brine (1×100 mL)
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resulting oil was purified by pressurized silica gel chromatography (40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-3ac466ddeeac4f499d6429a2fe03ba43
Source dataset
uspto-grants-2001_05
Patent number
US06232318B1

Reaction notes

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