Triethylamine → 5-Amino-7-chloro-3-(2,3,5'-tri-O-acetyl-beta-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2-one

HRID 2252406

Reaktionsgleichung

Reaktionsgleichung von HRID 2252406
[NH2:1][C:2]1[NH:3][C:4](=O)[C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:24][C@H:23]([CH2:25][O:26][C:27](=[O:29])[CH3:28])[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:13]3[O:14][C:15](=[O:17])[CH3:16])[C:6]=2[N:7]=1.C(N(CC)CC)C.O=P(Cl)(Cl)[Cl:40].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:3]=[C:4]([Cl:40])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:24][C@H:23]([CH2:25][O:26][C:27](=[O:29])[CH3:28])[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:13]3[O:14][C:15](=[O:17])[CH3:16])[C:6]=2[N:7]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 1354347855-amino-3-(2,3,5-tri-O-acetyl-beta-ribofuranosyl)thiazolo(4,5-d)pyrimidine-2,7-dione

Produkt 1

HCID 595339205-Amino-7-chloro-3-(2,3,5'-tri-O-acetyl-beta-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2-oneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of 25 (0.84 g, 1.90 mmol) in CHCl3 (9 mL) was added triethylamine (0.50 mL, 3.59 mmol) and POCl3 (1.60 mL, 17.1 mmol). After heating at reflux for 16 h, the reaction mixture was cooled to room temperature and poured onto ice and sat. aq. NaHCO3 (150 mL). The resulting mixture was extracted with CH2Cl2 (3×75 mL) and the combined organic layers dried (MgSO4). Concentration followed by flash chromatography (9:1/CH2Cl2:EtOAc) afforded 708 mg (87%) of product as a white solid, m.p. 101-103° C. 1H NMR (400 MHz, CDCl3) δ 6.10 (d, J=2.8 Hz, 1H), 6.01 (dd, J=5.6, 3.2 Hz, 1H), 5.92 (t, J=6.0 Hz, 1H), 5.42 (s, 2), 4.97 (dd, J=11.6, 3.6 Hz, 1H), 4.32 (m, 1), 4.21 (dd, J=12.0, 5.2 Hz, 1H), 2.12 (s, 6H), 2.06 (s, 3H).

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureat reflux for 16 h
  3. extractionThe resulting mixture was extracted with CH2Cl2 (3×75 mL)
  4. dry with materialthe combined organic layers dried (MgSO4)
  5. concentrationConcentration

Quellen und Nachweise

ORD-Eintrag
ord-3a872095617b4e24a68e46f6c395a85a
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07321033B2

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