6-Chloro-9-[(2R)-3,5-di-O-benzoyl-2-deoxy-2-fluoro-2-Methyl-b-D-erythro-pentofuranosyl]-9H-purin-2-aMine synthesis
- Product Name:6-Chloro-9-[(2R)-3,5-di-O-benzoyl-2-deoxy-2-fluoro-2-Methyl-b-D-erythro-pentofuranosyl]-9H-purin-2-aMine
- CAS Number:1199809-26-1
- Molecular formula:C25H21ClFN5O5
- Molecular Weight:525.92
1199809-24-9
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Yield:1199809-26-1 70%
Reaction Conditions:
Stage #1: 2-Amino-6-chloropurinwith potassium tert-butylate in tert-butyl alcohol; for 0.5 h;
Stage #2: (((2R,3R,4R,5R)-3-(benzoyloxy)-5-bromo-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate) in acetonitrile;tert-butyl alcohol at 50; for 16 h;
Steps:
12
To a suspension of 2-amine-6-chloro-9H-purine (1.45 g, 8.6 mmol) in t- BuOH(15 mL) was added t-BuOK (880 mg, 7.8 mmol) and stirred for 30 min. To this was added a solution of Intermediate 4 (((2R,3R,4R,5R)-3-(benzoyloxy)-5-bromo-4-fluoro-4- methyltetrahydrofuran-2-yl)methyl benzoate, 1.5 g, 3.4 mmol) in ACN (20 mL). The resulting solution was stirred for 16 h at 50 oC. The solution was cooled to R.T., the pH was adjusted to 7 with AcOH, then diluted with 100 mL of EA, washed with 2x50 mL of water. The resulting solution was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was applied onto a silica gel column with DCM/MeOH (50:1). This resulted in 1.26 g (70%) of compound 15-1 ((2S,3S,4R,5R)-5-(2,6-diamino-9H-purin-9- yl)-2,4-difluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol) as a yellow solid. ESI- MS: m/z 526 [M+H]+.
References:
WO2018/31818,2018,A2 Location in patent:Paragraph 0396
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10310-21-1
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1199809-26-1
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