Cesium carbonate → HCID 86645053, compound

HRID 1474030Notes

Reaction equation

HRID 1474030 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([Cl: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>[Cl: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 68457620HCID 68457620, compound

Product 1

HCID 86645053HCID 86645053, compoundYield 41%

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-chlorophenol (13 mg, 0.06 mmol) and Cs2CO3 (18 mg, 0.06 mmol) in acetone (1 mL) was treated with 4-bromo-2-methyl-2-butene (6.5 μL, 0.41 mmol) at room temperature. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 1/9) in 41% yield (7 mg).

Sources & evidence

ORD record
ord-3ddd0e09bc254df891c22cecfe1fbddd
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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