Tyrosol → HCID 67776411, compound

HRID 705899Notes

Reaction equation

HRID 705899 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][CH:15]=[CH:14][N:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:13]1[CH:14]=[CH:15][CH:16]=[N:17][C:12]=1[O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][OH:1])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 10393TyrosolHCID 11430Potassium CarbonateHCID 744042-Chloropyrimidine

Product 1

HCID 67776411HCID 67776411, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 4-(2-hydroxyethyl)phenol (950 mg, 6.88 mmol) in DMF (15 mL) was added 2-chloropyrimidine (750 mg, 6.55 mmol) and K2CO3 (1086 mg, 7.86 mmol). The mixture was heated at 110° C. overnight. Purification via reverse phase flash chromatography then afforded the title compound (1.3 g, 6.01 mmol, 92% yield). LCMS: rt=1.85 min, [M+H+]=218

Workup

  1. customPurification via reverse phase flash chromatography

Sources & evidence

ORD record
ord-a9f08922841543909a9ec3f3cb569756
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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