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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 373882Generated: October 30, 2026

Triethylamine → 4-Chloro-6-[[3-(diethoxyphosphoryl)propoxy]amino]-5-formamidopyrimidine

https://huagongshe.com/reaction/373882

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantN-(4,6-dichloropyrimidin-5-yl)formamideHCID 10932261—
ReactantDiethyl 3-(aminooxy)propylphosphonateHCID 19808651—
Solvent1,4-DioxaneHCID 31275—
Product4-Chloro-6-[[3-(diethoxyphosphoryl)propoxy]amino]-5-formamidopyrimidineHCID 1980865382.2%

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of 4,6-dichloro-5-formamidopyrimidine (2.82 g, 14.6 mmol), diethyl 3-(aminooxy)propylphosphonate (3.1 g, 14.6 mmol) and triethylamine (3.1 ml, 22.3 mmol) in dioxan (40 ml) was heated at 100° C. for 4 hours. The solution was cooled to ambient temperature, filtered, and the filtrate evaporated to give a yellow oil. The oil was purified by column chromatography on silica gel (eluting with chloroform: methanol 97:3) to give the title compound as a yellow oil (4.4 g, 74%). 1H NMR: δH (CDCl3) 1.3 (6H, t, J=7Hz, (OCH2CH3)2), 1.6-2.5 (4H, m, CH2CH2P), 3.9-4.5 (6H, m, N--OCH2, (OCH2CH3)2), 7.3-9.3 (3H, broad, --NHCHO, --NH--OCH2).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05166198
Source datasetuspto-grants-1992_11
ORD IDord-c054f13e5b37425e9f917ac3b204584e
Source noteuspto-grants-1992_11