Pyridine → Isotorabine

Participants

Role	Name	HCID	Charge
Reactant	Pyridine	HCID 1049	—
Reactant	5-Amino-3-(2',3'-di-O-acetyl, 5'-O-tert-butyl-dimethylsilanyl-beta-D-ribofuranosyl)-3H-thiazolo[4,5-d]pyrimidin-2-one	HCID 57673899	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	Isotorabine	HCID 11234476	100.5%

Reaction Steps

To a solution of 88 (0.22 g, 0.44 mmol) in THF (5 mL) in a plastic vial was added HF/pyridine (0.70 mL). The reaction was stirred for 2 h, concentrated and purified by flash column chromatography (silica, MeOH/CHCl3: gradient=5-10%) to afford 0.17 g (100%) of the title compound as a white solid: mp 109-111° C.; 1H (400 MHz, d6-DMSO) δ 8.37 (s, 1H), 6.91 (s, 2H), 6.00 (m, 2H), 5.48 (t, J=6.0 Hz, 1H), 4.91 (t, J=6.0 Hz, 1H), 4.04 (dd, J=10.4, 6.0 Hz, 1H), 3.64 (m, 1H), 3.52 (m, 1H), 2.08 (s, 3H), 2.05 (s, 3H); MS (+)-ES [M+H]+ m/z 385.3. Elemental Analysis calc'd for C14H16N4O7S.0.5 CH3OH.0.2 CHCl3: C, 41.61; H, 4.32; N, 13.21; S 7.56. Found: C, 41.73; H, 4.29; N, 12.86; S, 7.33.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07943759B2
Source dataset	uspto-grants-2011_05
ORD ID	ord-b569da09828748579db577138fe75993
Source note	uspto-grants-2011_05