Iodoethane → HCID 9922635, compound

HRID 984055Notes

Reaction equation

HRID 984055 reaction equation
C([O:3][C:4]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)[CH:9]=[CH:8][N:7]=1)=O)C.F[C:27]1C=CC(OC2C=CC(C3C=CN=C(C(O)=O)N=3)=CC=2)=CC=1.ICC.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][C:15]2[CH:16]=[CH:17][C:12]([C:10]3[CH:9]=[CH:8][N:7]=[C:6]([C:4](=[O:3])[CH3:27])[N:11]=3)=[CH:13][CH:14]=2)=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 9879709HCID 9879709, compoundHCID 68523248HCID 68523248, compound

Product 1

HCID 9922635HCID 9922635, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[4-(4-Fluorophenoxy)phenyl]-pyrimidine-2-carboxylic acid ethyl ester: A mixture of 4-[4-(4-fluorophenoxy)phenyl]-pyrimidine-2-carboxylic acid (3.15 g, 10.2 mmol), iodoethane (2.0 mL, 25 mmol), and cesium carbonate (7.00 g, 21.5 mmol) in DMF (100 mL) was maintained at 70°-80° C. for 16 hours. The mixture was then partitioned between water and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed 3 times with water, dried over sodium sulfate, filtered, and evaporated under reduced pressure to give an oil. Purification by column chromatography (1:1 hexane/ethyl acetate) afforded the desired product (2.14 g, 62%) as an oil which solidified upon standing at room temperature overnight, mp 61°-63° C. 1H NMR (CDCl3): δ 8.88 (d, J=5.4 Hz, 1H), 8.16 (d, J=8.7 Hz, 2H), 7.77 (d, J=5.4 Hz, 1H), 7.12-7.05 (m, 6H), 4.55 (q, J=7.5 Hz, 2H), 1.49 (t, J=7.5 Hz, 3H).

Workup

  1. temperaturewas maintained at 70°-80° C. for 16 hours
  2. customThe mixture was then partitioned between water and ethyl acetate
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. washThe combined organic layers were washed 3 times with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto give an oil
  9. customPurification by column chromatography (1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0eb9821a5e0445df8d6dd6d3c1a03767
Source dataset
uspto-grants-2005_03
Patent number
US06867210B2

Reaction notes

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