Cesium carbonate → N-[4-chloro-3-(3-methylbut-2-enoxy)phenyl]pyrimidin-2-amine

HRID 1474024Notes

Reaction equation

HRID 1474024 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][C:3]=1[OH:15].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:10]=[CH:11][CH:12]=[CH:13][N:14]=2)=[CH:4][C:3]=1[O:15][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 594749452-Chloro-5-(pyrimidin-2-ylamino)phenol

Product 1

HCID 15956123N-[4-chloro-3-(3-methylbut-2-enoxy)phenyl]pyrimidin-2-amineYield 53%

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-(pyrimidin-2-ylamino)phenol (30 mg, 0.14 mmol) and Cs2CO3 (47 mg, 0.14 mmol) in acetone (2.0 mL) was treated with 4-bromo-2-methyl-2-butene (16 μL, 0.14 mmol) at room temperature. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 7/3) in 53% yield (21 mg).

Sources & evidence

ORD record
ord-ab11515461234fa29f2fa5eb059b2ccf
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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