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Phosphate → HCID 67822659, Verbindung

HRID 1492466
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1492466
[H-].[Li+].[NH2:3][C:4]1[N:12]=[C:11]2[C:7]([NH:8][CH:9]=[N:10]2)=[C:6]([O:13][CH2:14][CH2:15][O:16][CH3:17])[N:5]=1.CS(O[C@H:23]1[CH2:27][CH2:26][C@H:25]([CH2:28][O:29][Si:30]([C:43]([CH3:46])([CH3:45])[CH3:44])([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:24]1[CH2:47][O:48][Si:49]([C:62]([CH3:65])([CH3:64])[CH3:63])([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)(=O)=O.P([O-])([O-])([O-])=O>CN(C=O)C.CO>[NH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[C@@H:23]2[CH2:27][CH2:26][C@H:25]([CH2:28][O:29][Si:30]([C:43]([CH3:45])([CH3:44])[CH3:46])([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C@H:24]2[CH2:47][O:48][Si:49]([C:62]([CH3:65])([CH3:64])[CH3:63])([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)=[C:6]([O:13][CH2:14][CH2:15][O:16][CH3:17])[N:5]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 1061PhosphateHCID 62714Lithium hydrideHCID 135468096-(2-Methoxyethoxy)-7H-purin-2-amineHCID 88444072HCID 88444072, Verbindung

Produkt 1

HCID 67822659HCID 67822659, VerbindungAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In an atmosphere of argon gas, lithium hydride (8.4 mg, 1.06 mmoles) was added to a suspension of 2-amino-6-(2-methoxyethoxy)purine (221 mg, 1.06 mmoles) in DMF (7 ml). After stirring the mixture for one hour, (1S,2S,3S)-2,3-bis(t-butyldiphenylsilyloxymethyl)-1-cyclopentyl methanesulfonate (370 mg, 0.53 mmole) was added, and the resulting mixture was stirred at 140° C. for one hour. After cooling the mixture, 0.2M phosphate buffer (pH 7) was added, and the product formed was extracted with ethyl acetate. The extract solution was washed with water, washed with saturated aqueous solution of sodium chloride and dried on anhydrous sodium sulfate, and then the solvent was distilled off. The residue was purified by silica gel column chromatography (methylene chloride:methanol=50:1, v/v) to obtain 2-amino-9-[(1R,2R,3S)-2,3-bis(t-butyldiphenylsilyloxymethyl)-1-cyclopentyl]-6-(2-methoxyethoxy)purine (124 mg, Yield 29%).

Aufarbeitung

  1. stirringthe resulting mixture was stirred at 140° C. for one hour
  2. additionwas added
  3. customthe product formed
  4. extractionwas extracted with ethyl acetate
  5. washThe extract solution was washed with water
  6. washwashed with saturated aqueous solution of sodium chloride
  7. dry with materialdried on anhydrous sodium sulfate
  8. distillationthe solvent was distilled off
  9. customThe residue was purified by silica gel column chromatography (methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-7312be4a5cab47549547ad4fc88cc255
Quelldatensatz
uspto-grants-1994_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05374625

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