Reacción #5965

Ecuación de reacción

Potassium carbonate

2-amino-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine

p-toluenesulphonic acid monohydrate

2,2-dimethoxypropane

→

2-amino-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine

Rendimiento 94.5%

Disolventes

Water

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe solution was stirred for a further 30 minutes
2. 2
   Extracciónthe solution was extracted with chloroform (3×8 ml)
3. 3
   Secadodried (magnesium sulphate)
4. 4
   Otrothe solvent removed

Procedimiento

To a suspension of 2-amino-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine (240 mg, 1.0 mmol) in N,N-dimethylformamide (3 ml) were added p-toluenesulphonic acid monohydrate (210 mg, 1.1 mmol) and 2,2-dimethoxypropane (0.62 ml, 5.0 mmol) and the solution was stirred for 30 minutes. Potassium carbonate (110 mg, 0.8 mmol) was added and the solution was stirred for a further 30 minutes. Water (10 ml) was added and the solution was extracted with chloroform (3×8 ml). The organic layers were combined, dried (magnesium sulphate) and the solvent removed. Trituration with toluene-ether afforded 2-amino-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine as a white crystalline solid (262 mg, 94%) which was recrystallised from ethyl acetate-hexane (216 mg, 78%), m.p. 118°-120°; λmax (MeOH) 221 (27,200), 244 (4,920), and 308 (7,130)nm; νmax (KBr) 3450, 3140, 1635, 1615, 1580, and 1435 cm-1 ; δH [(CD3)2SO] 1.26 (3H, s, CH3), 1.33 (3H, s, CH3), 1.58 (1H, m, 3'-H), 1.74 (2H, q, J 7.1 Hz, 2'-H), 3.54 (2H, dd, J 11.8 Hz and 8.5 Hz, 2×Hax), 3.78 (2H, dd, J 11.8 Hz and 4.4 Hz, 2×Heq), 4.07 (2H, t, J 7.2 Hz, 1'-H), 6.46 (2H, s, D2O exchangeable, 2-NH2), 8.09 (1H, s, 8-H), and 8.56 (1H, s, 6-H); (Found: C, 56.09; H, 6.91; N, 24.88%. C13H19N5O2 requires C, 56.30; H, 6.91; N, 25.25%).

Fuente