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

HRID 1880185Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[C:10]1[C:15]([C:16]2[CH2:17][CH2:18][O:19][CH2:20][CH:21]=2)=[CH:14][N:13]=[CH:12][N:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>O>[O:19]1[CH2:20][CH:21]=[C:16]([C:15]2[C:14]([O:8][C:5]3[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=3)=[N:13][CH:12]=[N:11][CH:10]=2)[CH2:17][CH2:18]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a 150 mL sealable tube was added 4-aminophenol (388 mg, 3.56 mmol), 4-chloro-5-(3,6-dihydro-2H-pyran-4-yl)pyrimidine (700 mg, 3.56 mmol), and cesium carbonate (1218 mg, 3.74 mmol) with DMSO (23.700 ml). The vessel was sealed and heated to 100° C. for 2 h. The reaction mixture was cooled to room temperature and diluted with water before extracting with ethyl acetate. The combined organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure to a dark brown oil that was used without purification. MS (ESI, pos. ion) m/z: 270.0 (M+1).

Workup

customThe vessel was sealed
temperatureThe reaction mixture was cooled to room temperature
extractionbefore extracting with ethyl acetate
dry with materialThe combined organics were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure to a dark brown oil that
customwas used without purification

Sources & evidence

ORD record: ord-9f0af0c872a94de4a9581f2e00468cec
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318718B2

Reaction notes

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