ChemicalBook CAS DataBase List 6-Chloro-9-[(2R)-3,5-di-O-benzoyl-2-deoxy-2-fluoro-2-Methyl-b-D-erythro-pentofuranosyl]-9H-purin-2-aMine

6-Chloro-9-[(2R)-3,5-di-O-benzoyl-2-deoxy-2-fluoro-2-Methyl-b-D-erythro-pentofuranosyl]-9H-purin-2-aMine synthesis

11synthesis methods

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 Synthesis

((2R,3R,4R,5R)-3-(benzoyloxy)-5-bromo-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate

1199809-24-9
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10310-21-1
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6-Chloro-9-[(2R)-3,5-di-O-benzoyl-2-deoxy-2-fluoro-2-Methyl-b-D-erythro-pentofuranosyl]-9H-purin-2-aMine

1199809-26-1
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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

1199809-24-9 Synthesis

1199809-24-9
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10310-21-1
546 suppliers
$10.00/5g

1199809-26-1
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References

1199809-24-9 Synthesis

1199809-24-9
2 suppliers
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10310-21-1
546 suppliers
$10.00/5g