4-(5-(3,6-Dihydro-2H-pyran-4-YL)pyrimidin-4-yloxy)aniline → 4-(5-(Tetrahydro-2H-pyran-4-YL)pyrimidin-4-yloxy)aniline

HRID 410321Notes

Reaction equation

[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:8]([O:13][C:14]3[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=3)=[N:9][CH:10]=[N:11][CH:12]=2)[CH2:3][CH2:2]1>[Pd].[OH-].[Pd+2].[OH-].C(O)C>[O:1]1[CH2:2][CH2:3][CH:4]([C:7]2[C:8]([O:13][C:14]3[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=3)=[N:9][CH:10]=[N:11][CH:12]=2)[CH2:5][CH2:6]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a pressure vessel was added palladium hydroxide, palladium on carbon (396 mg, 2.82 mmol), ethanol (18.800 ml), and 4-(5-(3,6-dihydro-2H-pyran-4-yl)pyrimidin-4-yloxy)aniline (760 mg, 2.82 mmol). The vessel was purged of air and backfilled with hydrogen (45 psi) before heating to 50° C. for 60 h. It was cooled to room temperature, filtered through Celite, and concentrated under reduced pressure to afford the product as a dark yellow oil. MS (ESI, pos. ion) m/z: 272.1 (M+1).

Workup

customThe vessel was purged of air
temperatureIt was cooled to room temperature
filtrationfiltered through Celite
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-967a9ac6a89b4ca3be89b6d3b62b77e2
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759532B2

Reaction notes

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