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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 969997Generated: October 30, 2026

Trifluoroacetic acid → 4-{2-[(3R)-1-azabicyclo[2.2.2]oct-3-yloxy]pyrimidin-5-yl}aniline

https://huagongshe.com/reaction/969997

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
Reactanttert-butyl 4-{2-[(3R)-1-azabicyclo[2.2.2]oct-3-yloxy]pyrimidin-5-yl}phenylcarbamateHCID 69430983—
Product4-{2-[(3R)-1-azabicyclo[2.2.2]oct-3-yloxy]pyrimidin-5-yl}anilineHCID 11220178—

Reaction Steps

The product of Example 19B (150 mg, 0.38 mmol) was treated with trifluroacetic acid (2 mL) according to the procedure of Example 18C. The title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.07) as solid (30 mg, yield, 26%). 1H NMR (300 MHz, MeOH-d4) δ 1.88-2.22 (m, 3H), 2.31-2.45 (m, 1H), 2.56-2.64 (m, 1H), 3.27-3.51 (m, 5H), 3.84-3.96 (m, 1H), 5.36-5.45 (m, 1H), 6.87 (d, J=8.5 Hz, 2H), 7.42 (d, J=8.5 Hz, 2H), 8.77 (s, 2H) ppm. MS (DCl/NH3) m/z 297 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07309699B2
Source datasetuspto-grants-2007_12
ORD IDord-06ba389f300f4e13bebec5c151d23ed9
Source noteuspto-grants-2007_12