Cesium carbonate → HCID 86645052, compound

HRID 1474029Notes

Reaction equation

HRID 1474029 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([CH3:16])=[C:13]([OH:15])[CH:14]=2)[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27]>CC(C)=O>[CH3:16][C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=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 68488712HCID 68488712, compound

Product 1

HCID 86645052HCID 86645052, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation of 2-R-5-(heteroaryl-2-ylamino)phenol, 5-(2-aminopyrimidin-4-ylamino)-2-methylphenol (89 mg, 0.41 mmol) and Cs2CO3 (134 mg, 0.41 mmol) in acetone (4.1 mL) was treated with 4-bromo-2-methyl-2-butene (50 μL, 0.41 mmol) at room temperature. The title compound was obtained after purification by flash chromatography on silica gel (CH2Cl2:MeOH 6/4) in 22% yield (26 mg).

Sources & evidence

ORD record
ord-4dd221952cab492587bb3fec390668f9
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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