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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2069072Generated: October 30, 2026

HCID 58416768, compound → 4-((4-Aminonaphthalen-1-yloxy)methyl)pyrimidin-2-amine

https://huagongshe.com/reaction/2069072

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHCID 58416768HCID 58416768—
ReactantHCID 178418361HCID 178418361—
CatalystPlatinumHCID 23939—
SolventAcetic AcidHCID 176—
SolventDichloromethaneHCID 6344—
Product4-((4-Aminonaphthalen-1-yloxy)methyl)pyrimidin-2-amineHCID 5841675591.1%

Reaction Steps

A solution of the nitroarene (70) (1.10 g, 3.71 mmol) in a mixture of DCM (50 mL) and AcOH (40 mL) was passed through a Thales H-cube (1.0 mL·min−1, 55 mm, 10% Pt/C, 40° C., full hydrogen mode). LC-MS analysis of the resulting solution showed a mixture comprising of mainly starting material and ca. 20% product. The DCM was removed by evaporation in vacuo and the solution re-subjected to reduction using the same conditions at RT. The volatiles were evaporated in vacuo to give the title compound (71) (ca. 70% by LC-MS) as a purple solid (0.90 g, 64% yield): m/z 267 (M+H)+ (ES+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08299073B2
Source datasetuspto-grants-2012_10
ORD IDord-92c393a23d914fbaafe61733020b5b19
Source noteuspto-grants-2012_10