Cesium carbonate → HCID 11537036, compound

HRID 1474033Notes

Reaction equation

HRID 1474033 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][N:10]=2)=[CH:4][C:3]=1[OH:17].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][N:10]=2)=[CH:4][C:3]=1[O:17][CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 684926902-Chloro-5-[(4-methoxypyrimidin-2-yl)amino]phenol

Product 1

HCID 11537036HCID 11537036, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation of 2-R-5-(heteroaryl-2-ylamino)phenol, 2-chloro-5-(4-methoxypyrimidin-2-ylamino)phenol (54 mg, 0.22 mmol) and Cs2CO3 (70 mg, 0.22 mmol) in acetone (3 mL) was treated with 4-bromo-2-methyl-2-butene (25 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 51% yield (35 mg).

Sources & evidence

ORD record
ord-620fb4eda1a547c88416536c47fce033
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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