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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1507477Generated: October 29, 2026

Triethylamine → (1S,2R,3R,5R)-3-(Hydroxymethyl)-5-(5-iodo-6-methoxy-2-(methylthio)pyrimidin-4-ylamino)cyclopentane-1,2-diol

https://huagongshe.com/reaction/1507477

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant(1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol HydrochlorideHCID 2734536—
ReactantHCID 117677754HCID 117677754—
SolventEthanolHCID 702—
Product(1S,2R,3R,5R)-3-(Hydroxymethyl)-5-(5-iodo-6-methoxy-2-(methylthio)pyrimidin-4-ylamino)cyclopentane-1,2-diolHCID 117677905—

Reaction Conditions

Temperature130 °C

Reaction Steps

Compound 3 (5.00 g, 15.7 mmol) and (1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol hydrochloride (Compound 4) (5.80 g, 31.6 mmol) were dissolved in EtOH (50 mL). Triethylamine (6.60 mL, 47.4 mmol) was added, the reaction was sealed, and heated to 130° C. for 18 h. The reaction mixture was cooled to room temperature and concentrated. The residue was purified via column chromatography on silica gel (EtOAc/hexanes) to give the title compound as a colorless oil. LCMS 1.23 min, 428 (M+H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09221809B2
Source datasetuspto-grants-2015_12
ORD IDord-6649a51ee5704c4b8bb8c8294eb35f19
Source noteuspto-grants-2015_12