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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 254750Generated: October 27, 2026

Acetic Acid → (6-Chloro-pyrimidin-4-yl)-(3-cyclopentyloxy-4-methoxy-benzyl)-amine

https://huagongshe.com/reaction/254750

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
Reactant4-Amino-6-chloropyrimidineHCID 238012—
Reactant3-Cyclopentyloxy-4-methoxybenzaldehydeHCID 2735893—
Solvent1,2-DichloroethaneHCID 11—
Product(6-Chloro-pyrimidin-4-yl)-(3-cyclopentyloxy-4-methoxy-benzyl)-amineHCID 8661429812.4%

Reaction Conditions

Temperature50 °C

Reaction Steps

Sodium tiracetoxyl-borohydride (985 mg, 4.65 mmol) was added to a solution of 6-chloro-pyrimidin-4-ylamine (200 mg, 1.55 mmol) and 3-cyclopentyloxy-4-methoxybenzaldehyde (682 mg, 3.1 mmol) in 25 ml of DCE. 1 ml of HOAc was added, and the mixture was stirred overnight at 50° C., followed by addition of 25 ml of DCE. The organic phase was washed with water, and the product was purified with column (silica gel, hexane:EtOAc 5:1) to give 64 mg of (6-chloro-pyrimidin-4-yl)-(3-cyclopentyloxy-4-methoxy-benzyl)-amine, yield 12%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07875622B2
Source datasetuspto-grants-2011_01
ORD IDord-66d91318115b45b683850b45a305e767
Source noteuspto-grants-2011_01