Dimethylbarbituric acid → HCID 69293381, compound

HRID 2113879Notes

Reaction equation

HRID 2113879 reaction equation
C([O:4][C:5]1[CH:19]=[CH:18][C:8]([CH2:9][O:10][CH2:11][CH2:12][N:13]2[N:17]=[CH:16][CH:15]=[N:14]2)=[CH:7][CH:6]=1)C=C.CN1C(=O)CC(=O)N(C)C1=O>ClCCl.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>[N:14]1[N:13]([CH2:12][CH2:11][O:10][CH2:9][C:8]2[CH:18]=[CH:19][C:5]([OH:4])=[CH:6][CH:7]=2)[N:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 69860Dimethylbarbituric acidHCID 69291040HCID 69291040, compound

Product 1

HCID 69293381HCID 69293381, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution of 950 mg (3.66 mmol) 2-[2-(4-allyloxy-benzyloxy)-ethyl]-2H-[1,2,3]-triazole in 20 ml dichloromethane was added to a solution of 1.71 g (11.0 mmol) 1,3-dimethylbarbituric acid and 104 mg (0.09 mmol) Pd(PPh3)4 in 40 ml dichloromethane and stirred for 4.5 h at 40° C. The mixture was extracted with 3×40 ml sat. NaHCO3-solution and 15 ml water and the combined aqueous phases were reextracted with 2×40 ml dichloromethane. The organic extracts were combined and dried over MgSO4. Solvents were distilled off and the residue purified by chromatography on silica gel (ethyl acetate/n-heptane 2:1) to yield 690 mg (86%) of the title compound.

Workup

  1. extractionThe mixture was extracted with 3×40 ml sat. NaHCO3-solution and 15 ml water
  2. dry with materialdried over MgSO4
  3. distillationSolvents were distilled off
  4. customthe residue purified by chromatography on silica gel (ethyl acetate/n-heptane 2:1)

Sources & evidence

ORD record
ord-f4dfa14130404f01bc39c6466f9b4645
Source dataset
uspto-grants-2008_10
Patent number
US07432291B2

Reaction notes

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