Reacción #367183

Ecuación de reacción

β-chloropropionaldehyde diethylacetal

2,4-diamino-5-(3-hydroxy-4,5-dimethoxybenzyl)pyrimidine

potassium t-butoxide

→

title compound

Rendimiento 83.0%

2,4-Diamino-5-(3-(3,3-diethoxypropoxy)-4,5-dimethoxybenzyl)pyrimidine

Rendimiento 83.0%

Disolventes

dimethyl sulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated at 65° overnight
2. 2
   OtroThe solvent was removed under vacuum
3. 3
   Otrothe residue was partitioned between 750 mL methylene chloride and 750 mL of 0.1N sodium hydroxide
4. 4
   OtroThe organic layer was separated
5. 5
   Extracciónthe aqueous layer was extracted with an additional 750 mL of methylene chloride
6. 6
   Lavadowashed with 750 mL of water
7. 7
   Secadodried (MgSO4)
8. 8
   Otropurified by flash column chromatography

Procedimiento

To a solution of 27.6 g, (0.1 mole) of 2,4-diamino-5-(3-hydroxy-4,5-dimethoxybenzyl)pyrimidine (D. E. Schwartz, W. Vetter, and G. Englert, Arzneim.-Forsch. (Drug Res.) 1970, 20, 1867; G. Rey-Bellet and R. Reiner, Helv. Chim. Acta 1970, 53, 945) in 400 mL of dry dimethyl sulfoxide was added 11.22 g (0.10 mole) of potassium t-butoxide. To the resulting suspension was added dropwise 17.92 g (0.107 mole) of β-chloropropionaldehyde diethylacetal. The mixture was heated at 65° overnight. The solvent was removed under vacuum and the residue was partitioned between 750 mL methylene chloride and 750 mL of 0.1N sodium hydroxide. The organic layer was separated and the aqueous layer was extracted with an additional 750 mL of methylene chloride. The organic layers were combined, washed with 750 mL of water, dried (MgSO4), and purified by flash column chromatography to yield 33.38 g (83%) of the title compound (mp 105°-106.5°). Anal. Calcd for C 20 H30N4O5 : C, 59.10; H, 7.44; N, 13.78. Found: C, 58.71; H, 7.40; N, 13.58.

Fuente