Dimethylbarbituric acid → HCID 54328958, compound

HRID 1584276Notes

Reaction equation

HRID 1584276 reaction equation
C([N:4]1[C@H:13]([CH2:14][N:15]2[C:19]([CH2:20][C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=3)=[CH:18][N:17]=[CH:16]2)[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)C=C.CN1C(=O)CC(=O)N(C)C1=O>C(Cl)Cl>[CH2:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:12][C@@H:13]([CH2:14][N:15]2[C:19]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([C:25]#[N:26])=[CH:27][CH:28]=3)=[CH:18][N:17]=[CH:16]2)[NH:4]1

Participants

4

Reactant 2

HCID 69860Dimethylbarbituric acidHCID 21311303HCID 21311303, compound

Product 1

HCID 54328958HCID 54328958, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

A solution of 4-{3-[2-(allyl)-(S)-1,2,3,4-tetrahydro-isoquinolin-3-yl-methyl]-3H-imidazol-4-yl-methyl}-benzonitrile (0.56 g, 1.52 mmol) in 7 ml degassed methylene chloride was added to palladium tetrakistriphenylphosphine (0.045 g, 0.04 mmol) and 1,3-dimethylbarbituric acid (0.712 g, 4.56 mmol) under argon atmosphere. The resulting solution was heated at 35° C. for 3 hr. The mixture was partitioned with methylene chloride, saturated sodium carbonate and water. The methylene chloride layer was dried with saturated sodium chloride and magnesium sulfate. The methylene chloride was removed in vacuo to obtain the title compound as an oil which was used in the next step without further purification.

Workup

  1. customThe mixture was partitioned with methylene chloride, saturated sodium carbonate and water
  2. dry with materialThe methylene chloride layer was dried with saturated sodium chloride and magnesium sulfate
  3. customThe methylene chloride was removed in vacuo

Sources & evidence

ORD record
ord-9c487b70b9a34dcab75887b7e1ec4e1e
Source dataset
uspto-grants-1999_08
Patent number
US05932590

Reaction notes

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