تفاعل #169426

معادلة التفاعل

(5-Amino-pyridin-3-yl)-{7-[3-(tert-butyl-dimethyl-silanyloxymethyl)-oxetan-3-yl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-methanone

(4-chloro-phenyl)-acetic acid

HATU

→

N-(5-{7-[3-(tert-butyl-dimethyl-silanyloxymethyl)-oxetan-3-yl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl}-pyridin-3-yl)-2-(4-chloro-phenyl)-acetamide

المردود 87.0%

المذيبات

pyridine

dichloromethane

sodium bicarbonate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was cooled to room temperature
2. 2
   workup.ADDITIONwas added
3. 3
   أخرىThe phases were separated
4. 4
   استخلاصthe aqueous layer was extracted with dichloromethane (3×5 mL)
5. 5
   تركيزThe combined organics were concentrated to dryness

الإجراء التجريبي

(5-Amino-pyridin-3-yl)-{7-[3-(tert-butyl-dimethyl-silanyloxymethyl)-oxetan-3-yl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-methanone (Preparation 216, 30 mg, 0.068 mmol) was dissolved in dry pyridine (2 mL) under nitrogen and to this was added (4-chloro-phenyl)-acetic acid (17 mg, 0.102 mmol), followed by HATU (39 mg, 0.102 mmol). The reaction was heated to 50° C. and stirred overnight. The reaction was cooled to room temperature, diluted with dichloromethane and saturated aqueous sodium bicarbonate was added. The phases were separated and the aqueous layer was extracted with dichloromethane (3×5 mL). The combined organics were concentrated to dryness to afford N-(5-{7-[3-(tert-butyl-dimethyl-silanyloxymethyl)-oxetan-3-yl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl}-pyridin-3-yl)-2-(4-chloro-phenyl)-acetamide as a pale yellow solid 35 mg, 87% yield.

المصدر