Cesium carbonate → 2-[(3-Methylbut-2-en-1-yl)oxy]-4-[(pyrimidin-2-yl)amino]benzonitrile

HRID 1474025Notes

Reaction equation

HRID 1474025 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:5][C:4]=1[OH:16])#[N:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27]>CC(C)=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:11]=[CH:12][CH:13]=[CH:14][N:15]=2)=[CH:5][C:4]=1[O:16][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])#[N:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 684876852-Cyano-5-(pyrimidin-2-ylamino)phenol

Product 1

HCID 159561222-[(3-Methylbut-2-en-1-yl)oxy]-4-[(pyrimidin-2-yl)amino]benzonitrileYield 30%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation of 2-R-5-(heteroaryl-2-ylamino)phenol, 2-cyano-5-(pyrimidin-2-ylamino)phenol (10 mg, 0.047 mmol) and Cs2CO3 (16 mg, 0.049 mmol) in acetone (2.0 mL) was treated with 4-bromo-2-methyl-2-butene (5.5 μL, 0.14 mmol) at room temperature. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 6/4) in 30% yield (4 mg).

Sources & evidence

ORD record
ord-b90f64d114df4c55b391315bb24847aa
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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