تفاعل #40610

معادلة التفاعل

triethylamine

8-indan-5-yl-2-methylsulfanyl-5-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

bromine

N2

→

solid

المردود 94.0%

8-Indan-5-yl-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

المردود 94.0%

المذيبات

CH2Cl2

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent was removed under vacuum
2. 2
   درجة الحرارةwithout heating
3. 3
   workup.DISSOLUTIONThe residue was redissolved in 2 mL of CH2Cl2
4. 4
   workup.STIRRINGThe solution was stirred at rt for 4 hours
5. 5
   أخرىThe solvent was evaporated
6. 6
   غسيلThe product was eluted with EtOAc/hexanes (1:5-1:2.5

الإجراء التجريبي

To a solution of 8-indan-5-yl-2-methylsulfanyl-5-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.32 g, 0.84 mmol) in 5 mL of methylene chloride (CH2Cl2) was added bromine (43 μL, 0.84 mmol) slowly under N2. The solution was stirred at room temperature for 2 hours (or to completion). The solvent was removed under vacuum without heating. The residue was redissolved in 2 mL of CH2Cl2, and was added triethylamine (234 μL, 1.68 mmol) in 1 mL of CH2Cl2. The solution was stirred at rt for 4 hours. The progress of the reaction was monitored by LC-MS. The solvent was evaporated and the residue was applied onto a silica gel column. The product was eluted with EtOAc/hexanes (1:5-1:2.5, v/v) and obtained as a white solid (0.30 g, 94%). 1H NMR (300 MHz, CDCl3) δ (ppm): 9.42 (s, 1H), 8.59 (s, 1H), 7.37 (d, J=7.8 Hz, 1H), 7.24 (s, 1H), 7.16 (d, J=7.8 Hz, 1H), 4.40 (q, 2H), 3.00 (m, 4H), 2.35 (s, 3H), 2.10 (m, 2H), 1.40 (t, 3H).

المصدر