Triphenylphosphine → HCID 86723883, compound

HRID 576776Notes

Reaction equation

HRID 576776 reaction equation
[O:1]=[C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]2[N:13]([C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)=[CH:4][N:3]1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1.[O:32]1[CH2:37][CH2:36][CH:35](O)[CH2:34][CH2:33]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[O:1]=[C:2]1[N:7]([CH:35]2[CH2:36][CH2:37][O:32][CH2:33][CH2:34]2)[C:6](=[O:8])[C:5]([C:9]2[N:13]([C:14]3[CH:15]=[CH:16][C:17]([C:18]#[N:19])=[CH:20][CH:21]=3)[N:12]=[CH:11][CH:10]=2)=[CH:4][N:3]1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:30])([F:29])[F:31])[CH:23]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86723884HCID 86723884, compound

Product 1

HCID 86723883HCID 86723883, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(5-(2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile (prepared in Example 53) (30 mg) in THF (2 ml) were added tetrahydro-2H-pyran-4-ol (0.014 ml), triphenylphosphine (37 mg) and diethyl azodicarboxylate (2.2 M toluene solution, 0.065 ml) and the resulting mixture was stirred at room temperature for fifteen minutes. The reaction solution was concentrated under reduced pressure and the residue was then purified by silica gel column chromatography (eluent: hexane/ethyl acetate) and reversed phase liquid chromatography (eluent: TFA water/acetonitrile) to afford-4-(5-(2,4-dioxo-3-(tetrahydro-2H-pyran-4-yl)-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile (7 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was then purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-814efbf8dcda490bad447b503e8371c7
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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