Cesium carbonate → HCID 15956127, compound

HRID 1474028Notes

Reaction equation

HRID 1474028 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([Cl:16])=[C:13]([OH:15])[CH:14]=2)[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27]>CC(C)=O>[Cl:16][C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:4]2[N:3]=[C:2]([NH2:1])[CH:7]=[CH:6][N:5]=2)=[CH:14][C:13]=1[O:15][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 68491242HCID 68491242, compound

Product 1

HCID 15956127HCID 15956127, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation of 2-R-5-(heteroaryl-2-ylamino)phenol, 5-(4-aminopyrimidin-2-ylamino)-2-chlorophenol (56 mg, 0.24 mmol) and Cs2CO3 (77 mg, 0.24 mmol) in acetone (3.0 mL) was treated with 4-bromo-2-methyl-2-butene (27 μL, 0.24 mmol) at room temperature. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 6/4) in 43% yield (31 mg).

Sources & evidence

ORD record
ord-538695b29aa1494686331da0a4506904
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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