تفاعل #62718

معادلة التفاعل

β-chloropropionaldehyde diethylacetal

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

potassium t-butoxide

→

title compound

المردود 83.0%

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

المردود 83.0%

المذيبات

dimethyl sulfoxide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was heated at 65° overnight
2. 2
   أخرىThe solvent was removed under vacuum
3. 3
   أخرىthe residue was partitioned between 750 mL methylene chloride and 750 mL of 0.1N sodium hydroxide
4. 4
   أخرىThe organic layer was separated
5. 5
   استخلاصthe aqueous layer was extracted with an additional 750 mL of methylene chloride
6. 6
   غسيلwashed with 750 mL of water
7. 7
   تجفيفdried (MgSO4)
8. 8
   أخرىpurified by flash column chromatography

الإجراء التجريبي

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 C20H30N4O5 : C, 59.10; H, 7.44; N, 13.78. Found: C, 58.71; H, 7.40; N, 13.58.

المصدر