4-Hydroxybenzaldehyde → HCID 86697014, compound

HRID 1626351Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[C:3]=1[CH3:22].[OH:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH:28]([C:27]1[CH:30]=[CH:31][C:24]([O:23][C:2]2[N:7]=[CH:6][N:5]=[C:4]([O:8][CH:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]3)[C:3]=2[CH3:22])=[CH:25][CH:26]=1)=[O:29]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of t-butyl 4-((6-chloro-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate (2.0 gm, 0.00610 mole) and 4-hydroxybenzaldehyde (1.34 gm, 0.00610 mole) in dimethyl formamide (50 mL), Cesium carbonate (4 gm, 0.0122 mole) was added and reaction mixture was stirred for 24 hours at 70° C. Then reaction mixture was cooled, poured into ice cold water and extracted with ethyl acetate. organic extract was washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure to yield crude product. The crude product so obtained was purified through column chromatography using 15-20% ethyl acetate in hexane to yield 1 gm product as oil.

Workup

customreaction mixture
customThen reaction mixture
temperaturewas cooled
additionpoured into ice cold water
extractionextracted with ethyl acetate
extractionorganic extract
washwas washed with water and brine
dry with materialdried over sodium sulfate
customevaporated under reduced pressure
customto yield crude product
customThe crude product so obtained
customwas purified through column chromatography

Sources & evidence

ORD record: ord-9ca9f2e8e873492a8e79564aa0464442
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785463B2

Reaction notes

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