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
Participants
| Role | Name | HCID | Charge |
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| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | N-(4,6-dichloropyrimidin-5-yl)formamide | HCID 10932261 | — |
| Reactant | Diethyl 3-(aminooxy)propylphosphonate | HCID 19808651 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-Chloro-6-[[3-(diethoxyphosphoryl)propoxy]amino]-5-formamidopyrimidine | HCID 19808653 | 82.2% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05166198 |
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| Source dataset | uspto-grants-1992_11 |
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| ORD ID | ord-c054f13e5b37425e9f917ac3b204584e |
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| Source note | uspto-grants-1992_11 |
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