Diisopropylethylamine → HCID 69289966, Verbindung

HRID 900061

Reaktionsgleichung

Reaktionsgleichung von HRID 900061
[I-].C(C[P+](C)(C)C)#N.[S:9]1[C:13]2[CH:14]=[C:15]([CH2:18]O)[CH:16]=[CH:17][C:12]=2[N:11]=[CH:10]1.[CH:20]1[NH:26][C:25]2[N:27]([C@@H:30]3[O:34][C@H:33]([CH2:35][OH:36])[C@@H:32]([OH:37])[C@H:31]3[OH:38])[CH:28]=[N:29][C:24]=2[C:22](=[S:23])[N:21]=1.CCN(C(C)C)C(C)C>C(#N)CC.O.CN(C=O)C>[S:9]1[C:13]2[CH:14]=[C:15]([CH2:18][S:23][C:22]3[N:21]=[CH:20][N:26]=[C:25]4[C:24]=3[N:29]=[CH:28][N:27]4[C@@H:30]3[O:34][C@H:33]([CH2:35][OH:36])[C@@H:32]([OH:37])[C@H:31]3[OH:38])[CH:16]=[CH:17][C:12]=2[N:11]=[CH:10]1

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 6761666-ThioinosineHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 178603856-(Hydroxymethyl)benzothiazole

Produkt 1

HCID 69289966HCID 69289966, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 7854PropionitrileLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

(Cyanomethyl)trimethylphosphonium iodide (45 mg) was added to a mixture of 40 (Burger, A.; Sawhney, S. N. J. Med. Chem. 1968, 11, 270-273) (33 mg, 0.2 mmol), 6-mercaptopurine riboside (42 mg, 0.2 mmol) and DIPEA (0.04 ml) in 0.43 ml of propionitrile. The mixture was heated at 90° C. and few drops of DMF were added to obtain a clear solution. Stirring was continued overnight at 90° C. The mixture was cooled to room temperature, water was added and slowly a pale brown precipitate was formed. The solid was collected and dried under vacuum. 1H NMR (CD3OD): δ9.20, 8.74 (2×s, 2H), 8.59 (s, 1), 8.18 (s, 1H), 7.98 (d, 1H, J=8.78 Hz), 7.67 (d, 1H, J=8.77 Hz), 6.07 (d, 1H, J=5.11 Hz), 4.84 (s, 2H), 4.72 (m, 1H), 4.35 (m, 1H), 4.17 (m, 2H), 3.83 (m, 1H);13C-NMR (CDCl3/d6-DMSO): 6161.5, 157.1, 153.5, 152.8, 149.5, 144.6, 137.4, 135.2, 129.0, 124.0, 123.7, 90.6, 87.6, 75.7, 72.2, 63.0, 33.2, 19.4; Mp=decomp. 140° C.; HRMS calc. for C18H18N5O4S2 m/Z=432.5100 (M+H), found 432.0787.

Aufarbeitung

  1. customto obtain a clear solution
  2. temperatureThe mixture was cooled to room temperature
  3. customslowly a pale brown precipitate was formed
  4. customThe solid was collected
  5. customdried under vacuum
  6. custom140° C.

Quellen und Nachweise

ORD-Eintrag
ord-a32a5ae7c8eb49d3b4cfa332c773d128
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07358235B2

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