تفاعل #66607

معادلة التفاعل

2-isopropyl-4,5-dimethoxy-benzaldehyde

4-chloro-5-iodo-2-methylsulfanyl-pyrimidine

isopropyl magnesium bromide

→

(4-chloro-2-methylsulfanyl-pyrimidin-5-yl)-(2-isopropyl-4,5-dimethoxy-phenyl)-methanol

المردود 82.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe mixture was quenched by the addition of brine
2. 2
   استخلاصextracted with CH2Cl2
3. 3
   تجفيفThe combined organic layers were dried over Na2SO4
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىPurification via flash chromatography (ethyl acetate)

الإجراء التجريبي

To a solution of 4-chloro-5-iodo-2-methylsulfanyl-pyrimidine (1.10 g, 3.9 mmol) in 20 mL THF at −40° C. was added isopropyl magnesium bromide (2.3 mL, 2 M in THF)) over 5 minutes. After 30 minutes, 2-isopropyl-4,5-dimethoxy-benzaldehyde from step 3 (1.04 g, 4.6 mmol) was added and the solution was warmed to room temperature. The mixture was quenched by the addition of brine, and extracted with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification via flash chromatography (ethyl acetate) afforded (4-chloro-2-methylsulfanyl-pyrimidin-5-yl)-(2-isopropyl-4,5-dimethoxy-phenyl)-methanol (1.168 g, 82%) as a light yellow solid.

المصدر