Tyrosol → HCID 67776441, compound

HRID 705898Notes

Reaction equation

HRID 705898 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl[C:12]1[N:17]=[CH:16][C:15]([Cl:18])=[CH:14][N:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:18][C:15]1[CH:14]=[N:13][C:12]([O:10][C:7]2[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][OH:1])=[CH:5][CH:6]=2)=[N:17][CH:16]=1

Participants

5

Reactant 3

HCID 10393TyrosolHCID 11430Potassium CarbonateHCID 5906412,5-Dichloropyrimidine

Product 1

HCID 67776441HCID 67776441, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 4-(2-hydroxyethyl)phenol (555 mg, 4.02 mmol) in DMF (15 mL) was added 2,5-dichloropyrimidine (570 mg, 3.83 mmol) and K2CO3 (635 mg, 4.59 mmol). The mixture was heated at 110° C. overnight. Purification via reverse phase flash chromatography then afforded the title compound (861 mg, 3.43 mmol, 90% yield). LCMS: rt=2.38 min, [M+H+]=251

Workup

  1. customPurification via reverse phase flash chromatography

Sources & evidence

ORD record
ord-ed53482cf0d14f6a9594ba24829345aa
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

Loading…