Acetone → HCID 11601905, compound

HRID 1474031Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2([NH2:15])C=CN=[CH:11][NH:10]2)=[CH:4][C:3]=1[OH:16].[C:17]([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27].[CH3:29][C:30](C)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:10]=[C:11]([CH3:17])[CH:30]=[CH:29][N:15]=2)=[CH:4][C:3]=1[O:16][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27]

Participants

Reactant 4

HCID 180Acetone

HCID 10796Cesium carbonate

HCID 700922-Butene, 1-bromo-3-methyl-

HCID 178508182HCID 178508182, compound

Product 1

HCID 11601905HCID 11601905, compoundYield 45%

Procedure

Following the general procedure for O-alkylation of 2-R-5-(heteroaryl-2-ylamino)phenol, 2-chloro-5-(4-aminopyrimidin-4-ylamino)phenol (53 mg, 0.22 mmol) and Cs2CO3 (73 mg, 0.22 mmol) in acetone (3 mL) was treated with 4-bromo-2-methyl-2-butene (26 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 45% yield (30 mg).

Sources & evidence

ORD record: ord-65216e40a4ac4f1182e065c78c72ffa1
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018209B2

Reaction notes

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