Tetrahydrofuran → 6-(1-Methyl-1H-pyrazol-4-yl)-2-[[3-[5-[2-(4-morpholinyl)ethoxy]-2-pyrimidinyl]phenyl]methyl]-3(2H)-pyridazinone

HRID 2042748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2042748
[OH:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([CH:25]=[CH:26][CH:27]=2)[CH2:11][N:12]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]([C:19]3[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=3)=[N:13]2)=[N:6][CH:7]=1.C1COCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:53][CH2:54][N:55]1[CH2:60][CH2:59][O:58][CH2:57][CH2:56]1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>>[CH3:24][N:22]1[CH:23]=[C:19]([C:14]2[CH:15]=[CH:16][C:17](=[O:18])[N:12]([CH2:11][C:10]3[CH:25]=[CH:26][CH:27]=[C:8]([C:5]4[N:6]=[CH:7][C:2]([O:1][CH2:53][CH2:54][N:55]5[CH2:60][CH2:59][O:58][CH2:57][CH2:56]5)=[CH:3][N:4]=4)[CH:9]=3)[N:13]=2)[CH:20]=[N:21]1

Komponenten

6

Edukt 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 5363146Diisopropyl azodicarboxylateHCID 59438049HCID 59438049, Verbindung

Produkt 1

HCID 251346926-(1-Methyl-1H-pyrazol-4-yl)-2-[[3-[5-[2-(4-morpholinyl)ethoxy]-2-pyrimidinyl]phenyl]methyl]-3(2H)-pyridazinone

Versuchsvorschrift

To a suspension of 360 mg (1.00 mmol) of 2-[3-(5-hydroxy-pyrimidin-2-yl)-benzyl]-6-(1-methyl-1H-pyrazol-4-yl)-2H-pyridazin-3-one in 2 ml THF 394 mg (1.50 mmol) of triphenylphosphine and 242 μl (2.00 mmol) of 4-(2-hydroxyethyl)morpholine are added one after the other. Under ice cooling 294 μl (1.50 mmol) of diisopropylazodicarboxylate are slowly added dropwise. The resulting solution is stirred for 18 hours at room temperature. The reaction mixture is then concentrated in vacuo and the oily residue is dissolved in 2-propanol. The resulting solid of 6-(1-methyl-1H-pyrazol-4-yl)-2-{3-[5-(2-morpholin-4-yl-ethoxy)-pyrimidin-2-yl]-benzyl}-2H-pyridazin-3-one resulted after some time is sucked off, washed with 2-propanol and tert-butylmethylether and dried in vacuo.

Aufarbeitung

  1. additionare added one after the other
  2. concentrationThe reaction mixture is then concentrated in vacuo
  3. dissolutionthe oily residue is dissolved in 2-propanol

Quellen und Nachweise

ORD-Eintrag
ord-41542f81f234402a8d820d2b9d6c6382
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586599B2

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