Triethylamine → 7-Chloro-2-(2-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidine

HRID 348008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 348008
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:18]=[C:11]2[N:12]=[C:13]([CH3:17])[CH:14]=[C:15](O)[N:10]2[N:9]=1.C(N(CC)CC)C.O=P(Cl)(Cl)[Cl:28].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:28][C:15]1[N:10]2[N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH:18]=[C:11]2[N:12]=[C:13]([CH3:17])[CH:14]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178429159HCID 178429159, Verbindung

Produkt 1

HCID 210837187-Chloro-2-(2-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a slurry of 2-(2-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-7-ol (I-1A-3f; 700 mg, 2.70 mmol) and triethylamine (0.57 ml, 4.0 mmol) in toluene (30 ml) at room temperature was added POCl3 (1.3 ml, 14 mmol), dropwise. The mixture was heated at 95° C. for 21 hours, cooled to room temperature, then slowly added to a stirred mixture of ice, saturated aqueous sodium bicarbonate and ethyl acetate. The aqueous layer was separated and extracted with additional ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), and then concentrated, in vacuo, to afford the crude product (0.79 g). Purification on a Biotage™ Flash 40S column using 0–20% ethyl acetate in hexanes as eluant afforded I-1A-3g as an off-white solid (643 mg, 86%): +ESI MS (M+1) 278.12; 1H NMR (400 MHz, CD2Cl2) δ 7.96–7.93 (m, 1H), 7.54–7.51 (m, 1H), 7.50–7.35 (m, 2H), 7.15 (s, 1H), 6.90 (s, 1H), 2.59 (s, 3H).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customThe aqueous layer was separated
  3. extractionextracted with additional ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated, in vacuo
  7. customto afford the crude product (0.79 g)
  8. customPurification on a Biotage™ Flash 40S column

Quellen und Nachweise

ORD-Eintrag
ord-79ae36246ee447cca58a24f69a7bae81
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176210B2

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