Reaktion #1195964

Reaktionsgleichung

4-bromobutyl acetate

7-amino-1H-1,3-azaphospholo[4,5-d]pyrimidine

7-Amino-1H-1,3-azaphospholo[4,5-d]pyrimidine

compound 10

7-Amino-1H-1,3-azaphospholo[4,5-d]pyrimidine

sodium hydride

→

title compound

Ausbeute 64.0%

7-Amino-1-(4-acetoxybutyl)-1,3-azaphospholo[4,5-d]pyrimidine

Ausbeute 64.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirring for 3 h
2. 2
   SonstigeDMF was evaporated
3. 3
   Sonstigethe residue was purified by chromatography over a silica gel column (2×15 cm)
4. 4
   Wascheneluted with dichloromethane containing 0-5% methanol
5. 5
   workup.ADDITIONThe homogeneous fractions containing the desired product
6. 6
   Sonstigewere collected
7. 7
   Sonstigeevaporated under reduced pressure

Vorschrift

To a suspension of 7-amino-1H-1,3-azaphospholo[4,5-d]pyrimidine (compound 10, 0.3 g, 2 mmol) in dry DMF (20 mL) was added sodium hydride (96 mg, 2.4 mmol) under an argon atmosphere. The mixture was stirred at ambient temperature for 30 min and 4-bromobutyl acetate (0.35 mL, 2.4 mmol) was added. After stirring for 3 h, DMF was evaporated and the residue was purified by chromatography over a silica gel column (2×15 cm). The column was flash eluted with dichloromethane containing 0-5% methanol. The homogeneous fractions containing the desired product were collected and evaporated under reduced pressure to yield 0.34 g (64%) of the title compound, mp 168-170° C. 31 p nmr (DMSO-d6): δ 62.34. 1H nmr (DMSO-d6): δ 1.56 (m, 2 H, CH2), 1.90 (m, 5 H, CH2, CH3), 4.00 (t, 2 H, NCH2), 4.30 (t, 2 H, CH2), 8.27 and 8.38 (2s, 2 H, NH2), 8.50 (d, 1 H, C5H), and 8.92 (d, 1 H, J =56.4 Hz, C2H ). Anal. Calcd. for C11H15N4O2P: C, 46.99; H, 5.43; N, 19.49. Found: C, 46.69; H, 5.44; N, 19.37.

Quelle