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ChemicalBook CAS DataBase List 4-chloro-7-[tris(1-methylethyl)silyl]-7H-Pyrrolo[2,3-d]pyrimidine
870706-50-6

4-chloro-7-[tris(1-methylethyl)silyl]-7H-Pyrrolo[2,3-d]pyrimidine synthesis

2synthesis methods
3680-69-1 Synthesis
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine

3680-69-1
808 suppliers
$6.00/1g

4-chloro-7-[tris(1-methylethyl)silyl]-7H-Pyrrolo[2,3-d]pyrimidine

870706-50-6
16 suppliers
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Yield:870706-50-6 100%

Reaction Conditions:

Stage #1: 4-chloro-1H-pyrrolo[2,3-d]pyrimidinewith n-butyllithium in tetrahydrofuran;hexane at -78 - 20; for 5.5 h;
Stage #2: with water;ammonium chloride in tetrahydrofuran;hexane;

Steps:

40.40A

Example 40; 40A. 4-Chloro-7-triisoDroDYlsilanyl-7H-Dyrrolo12,3-dlDyrimidine nBuLi (143 mL, 2.5 M in Hexane, 358 mmol) was added slowly to a solution of 4- Chloro-7H-pyrrolo[2,3-d]pyrimidine (50 g, 326 mmol) in THF (1.0 L) at -78 °C and stirred for 1 h. 3-tert-Butyl-3-chloro-2,2,4,4-tetramethyl-pentane (69.1 g, 358 mmol) was slowly added and the reaction mixture, stirred for 1.5 h at -78 °C , warmed to room temperature, and stirred for 3 h. The reaction mixture was quenched with 5% NH4CI (300 mL), concentrated in vacuo to remove THF, and extracted with CH2CI2 (4x500 mL). The combined organic extracts were filtered through silica gel and concentrated in vacuo to afford the title compound as a brown oil (100 g, 100%). MS: 310.1 (MH+); HPLC Rf: 9.40 min. (HPLC method 4).

References:

WO2005/116035,2005,A1 Location in patent:Page/Page column 63