Reacción #423239

Ecuación de reacción

2-Bromoethylbenzoate

NaH

ammonia

adenine

→

9-(2-hydroxyethyl)adenine

Disolventes

MeOH

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe mixture was then filtered
2. 2
   Otroto remove insoluble materiel
3. 3
   Otrothe filtrate was evaporated under reduced pressure
4. 4
   OtroThe residue was triturated with EtOAc
5. 5
   Filtraciónthen filtered
6. 6
   Otroto give a white solid, which
7. 7
   workup.STIRRINGThe reaction mixture was stirred for 14 h at room temperature
8. 8
   Otromethanol was removed under reduced pressure
9. 9
   OtroRecrystallization from EtOH afforded compound 2 (5.87 g, 85%)
10. 10
    Otromp 236° C. (Lit. 238-239° C.)

Procedimiento

To a suspension of 60% NaH in mineral oil (1.70 g, 42.57 mmol) in anhydrous DMF (120 mL) was added adenine (5.23 g, 38.70 mmol) under argon, and the mixture was heated at 60° C. for 1 h. 2-Bromoethylbenzoate (9.2 mL, 58.06 mmol) was added dropwise at 60° C., and the reaction was stirred at this temperature for 16 h. The mixture was then filtered to remove insoluble materiel, the filtrate was evaporated under reduced pressure and co-evaporated three times with toluene. The residue was triturated with EtOAc then filtered to give a white solid, which was immediately resuspended in a saturated ammonia solution in MeOH (400 mL). The reaction mixture was stirred for 14 h at room temperature, and then methanol was removed under reduced pressure. Recrystallization from EtOH afforded compound 2 (5.87 g, 85%): mp 236° C. (Lit. 238-239° C.); 1H NMR (DMSO-d6): 8.13 (s, 1H, H-2), 8.10 (s, 1H, H-8), 7.23 (bs, 2H, NH2), 5.05 (bs, 1H, OH), 4.19 (t, J=5.2 Hz, 2H, CH2O), 3.71 (t, J=5.2 Hz, 2H, CH2N). 13C NMR (DMSO-d6) δ: 155.79, 152.23, 149.44, 141.46, 118.55, 59.17, 45.61. MS (GT, FAB+): 136 (B+1H)+, 180 (M+1H)+, 202 (M+Na)+.

Fuente