Dimethylbarbituric acid → HCID 23614540, compound

HRID 1768070Notes

Reaction equation

HRID 1768070 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:12]([CH2:15][CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[N:18]2)(=[O:14])=[O:13])=[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:17]1([CH2:16][CH2:15][S:12]([CH2:11][C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:10][CH:9]=2)(=[O:14])=[O:13])[CH:21]=[CH:20][N:19]=[N:18]1

Participants

5

Reactant 2

HCID 69860Dimethylbarbituric acidHCID 23614531HCID 23614531, compound

Product 1

HCID 23614540HCID 23614540, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
40 °C

Procedure

A solution of 2.39 g (7.78 mmol) 1-[2-(4-allyloxy-phenylmethanesulfonyl)-ethyl]-1H-[1,2,3]triazole in 50 ml dichloromethane was added to a solution of 3.64 g (23.3 mmol) 1,3-dimethylbarbituric acid and 220 mg (0.19 mmol) Pd(PPh3)4 in 90 ml dichloromethane and stirred for 7 h at 40° C. The reaction mixture was washed with 3×80 ml sat. NaHCO3-solution, 2×30 ml water and the water phase extracted with 2×80 ml dichloromethane. The remaining precipitate was collected, washed with water and ethyl acetate and dried to yield. All dichloromethane fractions were combined, dried over 0.86 g of product. The aqueous phase from above was acidified by acetic acid to pH=5 and extracted with ethyl acetate. After washing with water and drying over sodium sulphate the ethyl acetate extract was evaporated to give 1.45 g of an orange powder that was purified by chromatography on silica gel (eluent:ethyl acetate) to yield an additional amount of 0.47 g product. Combined yield: 1.33 g (58%).

Workup

  1. washThe reaction mixture was washed with 3×80 ml sat. NaHCO3-solution, 2×30 ml water
  2. extractionthe water phase extracted with 2×80 ml dichloromethane
  3. customThe remaining precipitate was collected
  4. washwashed with water and ethyl acetate
  5. customdried
  6. customto yield
  7. dry with materialdried over 0.86 g of product
  8. extractionextracted with ethyl acetate
  9. washAfter washing with water
  10. dry with materialdrying over sodium sulphate the ethyl acetate
  11. extractionextract
  12. customwas evaporated

Sources & evidence

ORD record
ord-08aa31a713224a998d6762f2b434ea17
Source dataset
uspto-grants-2007_06
Patent number
US07235574B2

Reaction notes

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