Triphenylphosphine → 6-isopropyl-2-(3-{5-[1-(2-morpholin-4-ylethyl)-1H-pyrazol-4-yl]pyrimidin-2-yl}benzyl)-2H-pyridazin-3-one

HRID 1042005Notes

Reaction equation

HRID 1042005 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]2[CH:13]=[C:12]([C:14]3[CH:15]=[N:16][C:17]([C:20]4[CH:21]=[C:22]([CH2:26]O)[CH:23]=[CH:24][CH:25]=4)=[N:18][CH:19]=3)[CH:11]=[N:10]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH:28]([C:31]1[CH:32]=[CH:33][C:34](=[O:37])[NH:35][N:36]=1)([CH3:30])[CH3:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH:28]([C:31]1[CH:32]=[CH:33][C:34](=[O:37])[N:35]([CH2:26][C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([C:17]3[N:16]=[CH:15][C:14]([C:12]4[CH:11]=[N:10][N:9]([CH2:8][CH2:7][N:1]5[CH2:6][CH2:5][O:4][CH2:3][CH2:2]5)[CH:13]=4)=[CH:19][N:18]=3)[CH:21]=2)[N:36]=1)([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 230281476-Isopropyl-3-pyridazinoneHCID 58289705(3-{5-[1-(2-morpholin-4-ylethyl)-1H-pyrazol-4-yl]pyrimidin-2-yl}phenyl)methanol

Product 1

HCID 426416116-isopropyl-2-(3-{5-[1-(2-morpholin-4-ylethyl)-1H-pyrazol-4-yl]pyrimidin-2-yl}benzyl)-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.3 A solution, kept under nitrogen, of 324 mg (0.70 mmol) of (3-{5-[1-(2-morpholin-4-ylethyl)-1H-pyrazol-4-yl]pyrimidin-2-yl}phenyl)methanol, 131 mg (0.91 mmol) of 6-isopropyl-2H-pyridazin-3-one and 278 mg (1.05 mmol) of triphenylphosphine in 1.4 ml of THF is cooled in an ice bath, and 217 μl (1.056 mmol) of diisopropyl azodicarboxylate are added dropwise. After the reaction mixture has been stirred at room temperature for 2 hours, it is evaporated. The residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent, giving 6-isopropyl-2-(3-{5-[1-(2-morpholin-4-ylethyl)-1H-pyrazol-4-yl]pyrimidin-2-yl}benzyl)-2H-pyridazin-3-one (“A13”) as yellowish crystals; ESI 486;

Workup

  1. temperatureis cooled in an ice bath
  2. customit is evaporated
  3. customThe residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-b33e795d4c264cd898ecbd5ace8d42e4
Source dataset
uspto-grants-2013_10
Patent number
US08557813B2

Reaction notes

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