4-Chloro-6-[2-(diethoxyphosphorylmethoxy) ethoxyamino]-2,5-diformamidopyrimidine → 6-Chloro-9-[2-(diethoxyphosphorylmethoxy)ethoxy]-2-formamidopurine

HRID 6244

Reaktionsgleichung

Reaktionsgleichung von HRID 6244
[Cl:1][C:2]1[C:7]([NH:8][CH:9]=O)=[C:6]([NH:11][O:12][CH2:13][CH2:14][O:15][CH2:16][P:17]([O:22][CH2:23][CH3:24])([O:19][CH2:20][CH3:21])=[O:18])[N:5]=[C:4]([NH:25][CH:26]=[O:27])[N:3]=1>C(OC(OCC)OCC)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:25][CH:26]=[O:27])[N:5]=[C:6]2[C:7]=1[N:8]=[CH:9][N:11]2[O:12][CH2:13][CH2:14][O:15][CH2:16][P:17]([O:22][CH2:23][CH3:24])([O:19][CH2:20][CH3:21])=[O:18]

Komponenten

3

Edukt 1

HCID 148620634-Chloro-6-[2-(diethoxyphosphorylmethoxy) ethoxyamino]-2,5-diformamidopyrimidine

Produkt 1

HCID 148620676-Chloro-9-[2-(diethoxyphosphorylmethoxy)ethoxy]-2-formamidopurineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

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

Versuchsvorschrift

A solution of 4-chloro-6-[2-(diethoxyphosphorylmethoxy) ethoxyamino]-2,5-diformamidopyrimidine (2.8 g, 6.6 mmol) in diethoxymethyl acetate (20 ml) was heated at 120° C. for 2 hours. After cooling to ambient temperature, excess solvent was removed under reduced pressure, the residue dissolved in methanol (20 ml) and 0.880 ammonia (6.5 ml) and the solution stirred at ambient temperature for 1 hour. The solvent was evaporated to leave an oil which was chromatographed on silica gel (eluted with dichloromethane: methanol, 98.2) to give the title compound as a pale yellow oil (2.4 g, 90%). IR: νmax (film) 3480, 3120, 2995, 1710, 1610, 1580, 1510, 1440, 1390, 1330, 1240, 1050, 1030, 970, 920, 780 cm-1 ; 1H NMR δH [(CD3)2SO] 1.23 (6H, t, J=7 Hz, (OCH2CH3)2), 3.87 (2H, d, J=8 Hz, OCH 2P), 3.87 (2H, m, N-OCH2CH2), 4.03 (4H, m, (OCH2CH3)2), 4.56 (2H, m, N-OCH2CH2), 8.75 (1H, s, H-8), 9.38 (1H, br.s, CHO), 11.30 (1H, br.s, D2O exchangeable NHCHO). Found: C, 38.19; H, 4.79; N, 16.74%. C13H19N5O6PCl requires: C, 38.29; H, 4.70; N, 17.17%. Found: m/z 408.0827 (MH+). C13H20N5O6PCl requires: m/z 408.0840 (MH+).

Aufarbeitung

  1. customexcess solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in methanol (20 ml)
  3. customThe solvent was evaporated
  4. customto leave an oil which
  5. customwas chromatographed on silica gel (eluted with dichloromethane: methanol, 98.2)

Quellen und Nachweise

ORD-Eintrag
ord-97703c536bb449538d3e957266c1c6f1
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05247085

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