4-(1-t-Butyldimethylsilyloxy-3-diethoxyphosphorylmethoxyprop-2-oxyamino)-6-chloro-2,5-diformamidopyrimidine → HCID 54502642, Verbindung

HRID 345063

Reaktionsgleichung

Reaktionsgleichung von HRID 345063
[Si:1]([O:8][CH2:9][CH:10]([O:22][NH:23][C:24]1[C:29]([NH:30][CH:31]=O)=[C:28]([Cl:33])[N:27]=[C:26]([NH:34][CH:35]=[O:36])[N:25]=1)[CH2:11][O:12][CH2:13][P:14]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(OC(OC(=O)C)OCC)C>[Si:1]([O:8][CH2:9][CH:10]([O:22][N:23]1[CH:31]=[N:30][C:29]2[C:24]1=[N:25][C:26]([NH:34][CH:35]=[O:36])=[N:27][C:28]=2[Cl:33])[CH2:11][O:12][CH2:13][P:14]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3]

Komponenten

3

Edukt 1

HCID 1317170244-(1-t-Butyldimethylsilyloxy-3-diethoxyphosphorylmethoxyprop-2-oxyamino)-6-chloro-2,5-diformamidopyrimidine

Produkt 1

HCID 54502642HCID 54502642, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 84166Methanol, 1,1-diethoxy-, 1-acetateLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of 4-(1-t-butyldimethylsilyloxy-3-diethoxyphosphorylmethoxyprop-2-oxyamino)-6-chloro -2,5-diformamidopyrimidine (0.68 g, 1.19 mmol) in diethoxymethylacetate (10 ml) was stirred at 120° C. for 4 hours. The solvent was evaporated under high vacuum, the residue dissolved in methanol (10 ml) and 0.88 ammonia (0.3 ml) and stirred for 1 hour at 20° C. After evaporation to dryness, the residue was chromatographed on silica eluting with chloroform-methanol 40:1 affording 9-(1-t-butyldimethylsilyloxy-3-diethoxyphosphorylmethoxyprop-2-oxy)-6-chloro-2-formamidopurine (0.32 g, 49%) as a pale yellow oil. νmax (film) 3420, 1710, 1620, 1580, 1510, 1440, 1390, 1250 and 1030 cm-1 ; δH (CDCl3) 0.80(6H, s, (CH3)2Si), 0.87(9H, s, (CH3)3C), 1.30(6H, t, J7.2 Hz, 2×CH2CH3), 3.86(6H, m, CH2OSi+CH2OCH2P), 4.15(4H, m, 2×CH2CH3), 4.50(1H, m, CHON); 8.26(1H, s, H-8); 9.00(1H, br.d, J10.5 Hz, D2O exchangeable, NHCHO), 9.53(1H, d, J10.5 Hz, NHCHO). Found: C,43.02; H,6.49; N,12.18%; MH+ 552.1812. C20H35N5O7ClPSi.0.5H2O requires C,42.82; H,6.47; N,12.47%; MH+ 552.1810.

Aufarbeitung

  1. customThe solvent was evaporated under high vacuum
  2. dissolutionthe residue dissolved in methanol (10 ml)
  3. customAfter evaporation to dryness
  4. customthe residue was chromatographed on silica eluting with chloroform-methanol 40:1 affording 9-(1-t-butyldimethylsilyloxy-3-diethoxyphosphorylmethoxyprop-2-oxy)-6-chloro-2-formamidopurine (0.32 g, 49%) as a pale yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-87243a1a531f4df2a9214d14259fc4ae
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05055458

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