7H-Pyrrolo[2,3-d]pyrimidine, 2-chloro-4-(cyclopentyloxy)-5-(2-methyl-6-benzoxazolyl)-7-[[2-(trimethylsilyl)ethoxy]methyl]- synthesis

8synthesis methods

Product Name:7H-Pyrrolo[2,3-d]pyrimidine, 2-chloro-4-(cyclopentyloxy)-5-(2-methyl-6-benzoxazolyl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-
CAS Number:1618663-22-1
Molecular formula:C25H31ClN4O3Si
Molecular Weight:499.08

96-41-3
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7H-Pyrrolo[2,3-d]pyrimidine, 2,4-dichloro-5-(2-methyl-6-benzoxazolyl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-

1618663-21-0
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7H-Pyrrolo[2,3-d]pyrimidine, 2-chloro-4-(cyclopentyloxy)-5-(2-methyl-6-benzoxazolyl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-

1618663-22-1
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Yield:1618663-22-1 88%

Reaction Conditions:

with sodium t-butanolate in 1,3-dioxane at 70; for 3 h;Inert atmosphere;Sealed tube;

Steps:

3 6-(2-Chloro-4-(cyclopentyloxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole

A solution of 6-(2,4-dichloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole (1 equiv), cyclopentanol (1.1 equiv), and sodium tert-butoxide (1 equiv) in 1,4-dioxane (0.22 M) was taken in a sealable flask. The reaction mixture was put under a nitrogen atmosphere, the sealable flask was sealed and the mixture was stirred at 70° C. for 3 h. The mixture was cooled to room temperature and concentrated to afford an oil, which was suspended in DCM and loaded onto a silica column (packed with hexane). The column was eluted with 0-30% ethyl acetate in hexane. The fractions containing product were combined and concentrated to dryness to give the target product as a light yellow oil (Yield: 88%) that solidified upon standing. MS (ESI) m/z 499.4 [M+1]⁺

References:

US2014/200206,2014,A1 Location in patent:Paragraph 0232