Triphenylphosphine → 3-{1-[3-(5-Methylpyrimidin-2-yl)benzyl]-6-oxo-1,6-dihydropyridazin-3-yl}benzonitrile

HRID 1408392Notes

Reaction equation

HRID 1408392 reaction equation
[N+](C(OC(C)C)=O)(C(OC(C)C)=O)=[N-].[O:15]=[C:16]1[NH:21][N:20]=[C:19]([C:22]2[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=2)[C:25]#[N:26])[CH:18]=[CH:17]1.[CH3:30][C:31]1[CH:32]=[N:33][C:34]([C:37]2[CH:38]=[C:39]([CH2:43]O)[CH:40]=[CH:41][CH:42]=2)=[N:35][CH:36]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:30][C:31]1[CH:36]=[N:35][C:34]([C:37]2[CH:38]=[C:39]([CH:40]=[CH:41][CH:42]=2)[CH2:43][N:21]2[C:16](=[O:15])[CH:17]=[CH:18][C:19]([C:22]3[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=3)[C:25]#[N:26])=[N:20]2)=[N:33][CH:32]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 203265203-(6-Oxo-1,6-dihydropyridazin-3-yl)benzonitrileHCID 22145704Diisopropyl diazodicarboxylateHCID 59484945[3-(5-Methylpyrimidin-2-yl)phenyl]methanol

Product 1

HCID 594848913-{1-[3-(5-Methylpyrimidin-2-yl)benzyl]-6-oxo-1,6-dihydropyridazin-3-yl}benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8.3 147 μl (0.75 mmol) of diisopropyl diazodicarboxylate are added dropwise to a suspension of 98.6 mg (0.50 mmol) of 3-(6-oxo-1,6-dihydropyridazin-3-yl)benzonitrile, 100 mg (0.50 mmol) of [3-(5-methylpyrimidin-2-yl)phenyl]methanol and 197 mg (0.75 mmol) of triphenylphosphine in 3 ml of THF, and the resultant solution is stirred at room temperature for 18 hours. The reaction mixture is evaporated in vacuo, and 2-propanol is added to the residue. The resultant precipitate is filtered off with suction and chromatographed on a silica gel column with dichloromethane/methanol as eluent: 3-{1-[3-(5-methylpyrimidin-2-yl)benzyl]-6-oxo-1,6-dihydropyridazin-3-yl}benzonitrile (“A15”) as yellowish solid; ESI 380;

Workup

  1. customThe reaction mixture is evaporated in vacuo, and 2-propanol
  2. additionis added to the residue
  3. filtrationThe resultant precipitate is filtered off with suction
  4. customchromatographed on a silica gel column with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-0258cf21d3de434b872b5784d05811f8
Source dataset
uspto-grants-2014_12
Patent number
US08921357B2

Reaction notes

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