Cesium carbonate → HCID 15956126, compound

HRID 1474032Notes

Reaction equation

HRID 1474032 reaction equation
N[CH2:2][O:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([CH3:18])=[C:15]([OH:17])[CH:16]=2)[N:5]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:26][CH:27]=[C:28]([CH3:30])[CH3:29]>CC(C)=O>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([CH3:18])=[C:15]([O:17][CH2:26][CH:27]=[C:28]([CH3:30])[CH3:29])[CH:16]=2)[N:5]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 68493912HCID 68493912, compound

Product 1

HCID 15956126HCID 15956126, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation of 2-R-5-(heteroaryl-2-ylamino)phenol, 5-(4-aminomethoxypyrimidin-2-ylamino)-2-methylphenol (15 mg, 0.07 mmol) and Cs2CO3 (21 mg, 0.07 mmol) in acetone (1 mL) was treated with 4-bromo-2-methyl-2-butene (7.5 μL, 0.22 mmol) at room temperature. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAC 8/2) in 62% yield (12 mg).

Sources & evidence

ORD record
ord-d208540a36b3420db29f28bee55dc61e
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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