Tributylphosphine → HCID 59351665, compound

HRID 1889355Notes

Reaction equation

HRID 1889355 reaction equation
[CH2:1]([C:3]1[S:28][C:6]2[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:16][CH:15]=3)[C:8](=[O:12])[NH:9][C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC.[CH3:60][O:61][C:62]1[CH:67]=[CH:66][C:65]([C:68]2([CH2:71]O)[CH2:70][CH2:69]2)=[CH:64][CH:63]=1>O1CCCC1>[CH2:1]([C:3]1[S:28][C:6]2[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:16][CH:15]=3)[C:8](=[O:12])[N:9]([CH2:71][C:68]3([C:65]4[CH:64]=[CH:63][C:62]([O:61][CH3:60])=[CH:67][CH:66]=4)[CH2:70][CH2:69]3)[C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 18516144[1-(4-Methoxyphenyl)cyclopropyl]methanolHCID 593517704'-[(6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]biphenyl-2-carbonitrile

Product 1

HCID 59351665HCID 59351665, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4′-[(6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]biphenyl-2-carbonitrile (1 g), 1,1′-(azodicarbonyl)dipiperidine (1.3 g), tributylphosphine (1.6 mL), [1-(4-methoxyphenyl)cyclopropyl]methanol (0.46 g) and tetrahydrofuran (30 mL) was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure, to the residue was added diisopropyl ether (50 mL), and the mixture was stirred at room temperature for 1 hr. Insoluble material was filtered off, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.71 g, 50%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, to the residue
  2. additionwas added diisopropyl ether (50 mL)
  3. stirringthe mixture was stirred at room temperature for 1 hr
  4. filtrationInsoluble material was filtered off
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e0c7c0e9833a4deabaa317fb9c71239a
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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