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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 721374Generated: October 30, 2026

4-Hydroxymethylpyridine → HCID 21890695, compound

https://huagongshe.com/reaction/721374

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-HydroxymethylpyridineHCID 11472—
ReactantTriphosgeneHCID 94429—
ReactantSodium BicarbonateHCID 516892—
Reactant4-(6,7-Dimethoxyquinazolin-4-yloxy)anilineHCID 11616363—
SolventTolueneHCID 1140—
SolventDichloromethaneHCID 6344—
SolventTriethylamineHCID 8471—
ProductHCID 21890695HCID 2189069528.9%

Reaction Steps

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (50 mg) was added to toluene (5 ml), and triethylamine (0.5 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (77 mg) in methylene chloride was then added thereto, and the mixture was heated under reflux for 10 min. Next, 4-pyridylmethanol (28 mg) was added thereto, and the mixture was further stirred with heating under reflux for 3 hr. A saturated aqueous sodium bicarbonate solution was added to stop the reaction, and the reaction solution was then extracted with chloroform, and the extract was washed with water and saturated brine in that order. The extract was dried over sodium sulfate and was then concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (21 mg, yield 23%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07135466B2
Source datasetuspto-grants-2006_11
ORD IDord-392c82c1cdbf416abccb53a0371691d4
Source noteuspto-grants-2006_11