Water → HCID 62477123, compound

HRID 1855420Notes

Reaction equation

HRID 1855420 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Cl:9][C:10]1[N:15]=[C:14](Cl)[CH:13]=[C:12]([CH3:17])[N:11]=1.O>O1CCCC1>[Cl:9][C:10]1[N:15]=[C:14]([O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:13]=[C:12]([CH3:17])[N:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 97324-FluorophenolHCID 794712,4-Dichloro-6-methylpyrimidine

Product 1

HCID 62477123HCID 62477123, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

4-Fluorophenol (103 mg, 0.92 mmol) and potassium-tert-butylate (113 mg, 1.0 mmol) were dissolved in 7 mL of tetrahydrofurane. 2,4-dichloro-6-methylpyrimidine (150 mg, 0.92 mmol) was added and the mixture stirred at 20° C. overnight. Water was added and the mixture extracted with diethyl ether. Chromatography of the crude reaction product on silica gel using a heptane/ethyl acetate as an eluent gave the title compound (150 mg, 68%) as a slightly yellow solid. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.50-7.40 (m, 2H), 7.28 (t, 1H), 7.14 (d, 2H), 6.57 (s, 1H), 2.47 (s, 3H).

Workup

  1. extractionthe mixture extracted with diethyl ether
  2. customChromatography of the crude reaction product on silica gel using a heptane/ethyl acetate as an eluent

Sources & evidence

ORD record
ord-c71af14e56254b25a5597a8e40293093
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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