ChemicalBook CAS DataBase List 2-Chloro-4-(cyclopentyloxy)-5-iodo-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidine

2-Chloro-4-(cyclopentyloxy)-5-iodo-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidine synthesis

4synthesis methods

Product Name:2-Chloro-4-(cyclopentyloxy)-5-iodo-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidine
CAS Number:1618663-33-4
Molecular formula:C17H25ClIN3O2Si
Molecular Weight:493.84

96-41-3
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7-((2-(triMethylsilyl)ethoxy)Methyl)-2,4-dichloro-5-iodo-7H-pyrrolo[2,3-d]pyriMidine

1404364-72-2
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2-Chloro-4-(cyclopentyloxy)-5-iodo-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidine

1618663-33-4
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Yield:1618663-33-4 46%

Reaction Conditions:

Stage #1: Cyclopentanolwith sodium hydride in tetrahydrofuran;mineral oil at 0 - 20; for 0.5 h;Inert atmosphere;
Stage #2: 2,4-dichloro-5-iodo-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine in tetrahydrofuran;mineral oil at 20; for 4 h;Inert atmosphere;

Steps:

7 2-Chloro-4-(cyclopentyloxy)-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

To a solution of cyclopentanol (1 equiv) in anhydrous THF (0.22 M) was added sodium hydride (60% in mineral oil, 1.3 equiv) at 0° C. under nitrogen. After the resulting reaction mixture was stirred at room temperature for 30 min, 2,4-dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (0.67 equiv) was added. The reaction was stirred at room temperature for 4 h and quenched with saturated aqueous ammonium chloride solution. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. Concentration under vacuum gave the crude product, which was purified by silica gel column chromatography (5% ethyl acetate in petroleum ether) to afford the title compound (46% yield). MS (ESI) m/z 493.2. [M+1]⁺.

References:

US2014/200206,2014,A1 Location in patent:Paragraph 0253

2,4-Dichloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

1012785-51-1
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1618663-33-4
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References

90213-66-4
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1618663-33-4
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References

76513-69-4 Synthesis

76513-69-4
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1618663-33-4
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References