Dimethyl Sulfoxide → 3-[4-(3-Phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]propanal

HRID 856005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 856005
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]1([C:17]2[CH:18]=[N:19][N:20]3[CH:25]=[C:24]([C:26]4[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][CH2:34][OH:35])=[CH:28][CH:27]=4)[CH:23]=[N:22][C:21]=23)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[C:11]1([C:17]2[CH:18]=[N:19][N:20]3[CH:25]=[C:24]([C:26]4[CH:27]=[CH:28][C:29]([CH2:32][CH2:33][CH:34]=[O:35])=[CH:30][CH:31]=4)[CH:23]=[N:22][C:21]=23)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 586915973-[4-(3-Phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]propan-1-ol

Produkt 1

HCID 586916073-[4-(3-Phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]propanal

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Dimethylsulfoxide (0.862 mL, 12.2 mmol, 5.00 equiv) was added to a solution of oxalyl chloride (0.636 mL, 7.29 mmol, 3.00 equiv) in dichloromethane (10 mL) at −78° C. The mixture was stirred for 15 minutes before a solution of 3-[4-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]propan-1-ol (2-4, 0.800 g, 2.43 mmol, 1 equiv) in dichloromethane (100 mL) was added via cannula over 5 minutes. The resulting mixture was stirred at −78° C. for 1 hour. Triethylamine (3.50 mL, 25.1 mmol, 10.3 equiv) was added, and the mixture was then warmed to 0° C. and stirred for 30 minutes. The reaction mixture was partitioned between saturated sodium bicarbonate solution (100 mL) and additional dichloromethane (100 mL). The organic layer was dried over sodium sulfate and concentrated to give 3-[4-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)phenyl]propanal (2-5) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ9.86 (t, 1H, J=1.2 Hz), 8.82 (d, 1H, J=2.4 Hz), 8.81 (d, 1H, J=2.4 Hz), 8.46 (s, 1H), 8.06 (br d, 2H, J=7.8 Hz), 7.54 (d, 2H, J=8.2 Hz), 7.47 (t, 2H, J=7.8 Hz), 7.37 (d, 2H, J=8.2 Hz), 7.29 (t, 1H, J=7.8 Hz), 3.05 (t, 2H, J=7.1 Hz), 2.86 (t, 2H, J=7.1 Hz).

Aufarbeitung

  1. additionwas added via cannula over 5 minutes
  2. temperaturethe mixture was then warmed to 0° C.
  3. stirringstirred for 30 minutes
  4. customThe reaction mixture was partitioned between saturated sodium bicarbonate solution (100 mL) and additional dichloromethane (100 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5b3ea09b485b4e5eabb19b041a8b9ff4
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07262199B2

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