Dimethylbarbituric acid → HCID 23131006, compound

HRID 493716Notes

Reaction equation

HRID 493716 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([CH2:15][CH2:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([C:25]3[S:29]/[C:28](=[N:30]\C(=O)OCC=C)/[N:27]([CH3:37])[CH:26]=3)[CH2:21][CH2:20]1)=[O:18])(=[O:14])=[O:13])[CH:6]=[CH:5]2.CN1C(=O)CC(=O)N(C)C1=O>C1COCC1.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>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([CH2:15][CH2:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([C:25]3[S:29][C:28](=[NH:30])[N:27]([CH3:37])[CH:26]=3)[CH2:21][CH2:20]1)=[O:18])(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 69860Dimethylbarbituric acidHCID 140536539HCID 140536539, compound

Product 1

HCID 23131006HCID 23131006, compoundYield 62.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of allyl (2Z)-5-(1-(3-((6-chloro-2-naphthyl)sulfonyl)propanoyl)-4-piperidinyl)-3-methyl-1,3-thiazol-2(3H)-ylidenecarbamate (0.60 g) obtained in Example 57d) in THF, 1,3-dimethylbarbituric acid (0.25 g) and tetrakis(triphenylphosphine)palladium (0.06 g) were added thereto and mixed for 12 hours under argon atmosphere. The insolubles were filtered off, and the filtrate was concentrated. The residue was purified with a silica gel column to give the title compound (0.32 g) as a pale yellow solid.

Workup

  1. additionmixed for 12 hours under argon atmosphere
  2. filtrationThe insolubles were filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified with a silica gel column

Sources & evidence

ORD record
ord-39bd1d007bf54cc289b182fa7f980bb8
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Reaction notes

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