HCID 90111508, compound → HCID 90110526, compound

HRID 521717Notes

Reaction equation

HRID 521717 reaction equation
C([N:4]1[CH2:11][CH:10]2[C:6]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)([NH:7][O:8][CH2:9]2)[CH2:5]1)C=C>C(Cl)(Cl)Cl.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[CH:15]=[CH:16][CH:17]=[C:12]([C:6]23[CH2:5][NH:4][CH2:11][CH:10]2[CH2:9][O:8][NH:7]3)[CH:13]=1

Participants

4

Reactant 1

HCID 90111508HCID 90111508, compound

Product 1

HCID 90110526HCID 90110526, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6212ChloroformSolvent

Procedure

5-Allyl-6a-(3-pyridyl)-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole (2.14 g, 7.40 mmol) and N,N-dimethylbarbituric acid (6.93 g, 44.41 mmol) are dissolved in chloroform (80 mL) and the resulting solution is degassed twice using liquid nitrogen. Tetrakis(triphenylphosphine)palladium (1.28 g, 1.11 mmol) is added and the mixture is stirred at room temperature for 2 hours. The reaction is concentrated under reduced pressure. The resulting residue is dissolved in a 1:1 mixture of dimethylsulfoxide/methanol (40 ml) and the solution is loaded on an ion exchange column. The material is eluted with methanol (70 mL) then with 7 M ammonia/methanol solution (70 mL). The basic fraction is collected and concentrated under reduced pressure. The product is further purified by silica gel column chromatography using a 0-15% gradient of 0.14 M ammonia/methanol solution in dichloromethane to give the title compound (1.28 g, 86%). ES/MS (m/e): 192 (M+1).

Workup

  1. customthe resulting solution is degassed twice
  2. concentrationThe reaction is concentrated under reduced pressure
  3. dissolutionThe resulting residue is dissolved in a 1:1 mixture of dimethylsulfoxide/methanol (40 ml)
  4. washThe material is eluted with methanol (70 mL)
  5. customThe basic fraction is collected
  6. concentrationconcentrated under reduced pressure
  7. customThe product is further purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bda649ca9ca54d27bfbe1c369dc187a5
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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