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

HRID 410320
Notes
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Reaction equation

HRID 410320 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4034-AminophenolHCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 593268324-chloro-5-(3,6-dihydro-2H-pyran-4-yl)pyrimidine

Product 1

HCID 593269884-(5-(3,6-Dihydro-2H-pyran-4-YL)pyrimidin-4-yloxy)aniline

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

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

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

Sources & evidence

ORD record
ord-dd1912f6ced94d329a437b1064e320a5
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08759532B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes