Triethylamine → 9-(2-Phthalimidoethoxymethyl)guanine hydrate

HRID 848104Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 848104
C[Si]([C:5]1[NH:13][C:12]2[C:11](=[O:14])[NH:10][C:9]([N:15]([Si](C)(C)C)[Si](C)(C)C)=[N:8][C:7]=2[N:6]=1)(C)C.Cl[CH2:25][O:26][CH2:27][CH2:28][N:29]1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(O)C>[OH2:14].[C:30]1(=[O:39])[N:29]([CH2:28][CH2:27][O:26][CH2:25][N:6]2[CH:5]=[N:13][C:12]3[C:11](=[O:14])[NH:10][C:9]([NH2:15])=[N:8][C:7]2=3)[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]12

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 12926790N-(2-chloromethoxyethyl)phthalimideHCID 136139236Tris-(trimethylsilyl)guanine

Produkt 1

HCID 1363987959-(2-Phthalimidoethoxymethyl)guanine hydrateAusbeute 172,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a stirred solution of tris trimethylsilylguanine (16.5 g) in toluene (50 ml) was added N-(2-chloromethoxyethyl)phthalimide (17.0 g) and triethylamine (23 ml). The reaction mixture was heated at reflux under nitrogen for 29 hours, cooled and evaporated under reduced pressure giving a dark brown oil. The oil was digested in ethanol (400 ml) on a steam bath for 40 minutes, giving a solid which was collected and washed with ethanol and ether. It was recrystallized from 2-methoxyethanol to give 9-(2-phthalimidoethoxymethyl)guanine hydrate (14.4 g), m.p. >240° C. (dec.). A mixture of 9-(2-phthalimidoethoxymethyl)guanine hydrate (0.94 g), hydrazine (2 ml) and ethanol (100 ml) was heated at reflux with stirring for one hour. The reaction mixture was filtered hot, and the filtrate was cooled and evaporated under reduced pressure. Ethanol was added and the mixture re-evaporated. This was repeated three times. The residual solid was stirred with 3% aqueous acetic acid (50 ml) for 30 minutes and filtered. The solids were washed with water (15 ml), and the wash and filtrate combined. The combined wash and filtrate was evaporated under reduced pressure at <35° C. to a small volume, diluted with ethanol and evaporated to dryness. The pasty, white solid was dispersed in a small amount of ethanol and diluted with a few ml ether to give a granular solid which was collected, washed with ethanol and dried. Recrystallization from ethanol-water gave 9-(2-aminoethoxymethyl)guanine acetate monohydrate (0.43 g), m.p. (~135° C. melts and resolidifies) 174°-176° C.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under nitrogen for 29 hours
  3. temperaturecooled
  4. customevaporated under reduced pressure
  5. customgiving a dark brown oil
  6. customgiving a solid which
  7. customwas collected
  8. washwashed with ethanol and ether
  9. customIt was recrystallized from 2-methoxyethanol

Quellen und Nachweise

ORD-Eintrag
ord-231f919bf8b147a1a910999beae070f9
Quelldatensatz
uspto-grants-1981_10
Patentnummer
US04294831

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