Ammonia → HCID 135427937, compound

Participants

Role	Name	HCID	Charge
Reactant	Ammonia	HCID 222	—
Reactant	5-Amino-3-(2',3',5'-tri-O-benzoyl-2'-C-methyl-beta-D-ribofuranosyl)-3H,6H-thiazolo[4,5-d]pyrimidine-2,7-dione	HCID 136131607	—
Solvent	Methanol	HCID 887	—
Product	HCID 135427937	HCID 135427937	34%

Reaction Steps

A mixture of nucleoside triester 119 (209 mg, 0.325 mmol) and MeOH (10 mL) saturated with NH3 (g) at −30° C. was stirred in a sealed tube for 48 h. The mixture was warmed to rt, depressurized, concentrated then submitted to HPLC purification (MeCN—H2O), affording 36 mg (34%) of the title compound as a white solid after lyophilization: 1H (400 MHz, DMSO-d6) δ 11.18 (s, 1H), 6.92 (br s, 2H), 5.95 (s, 1H), 5.18-5.28 (br m, 1H), 4.75 (br s, 1H), 4.53 (dd, J=11.3, 5.46, 1H), 3.95 (br s, 1H), 3.73-3.78 (m, 1H), 3.29 (br s, 2H), 1.04 (s, 3H); [M+H]+ m/z 331.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08883758B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-18541b0cfcf14f23ba1cfa2e6b895ec1
Source note	uspto-grants-2014_11