Diisopropylethylamine → HCID 66955906, compound

HRID 1399592Notes

Reaction equation

HRID 1399592 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:12]([CH3:19])[N:11]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.Br[CH2:27][O:28][CH3:29].[CH:30](N(CC)C(C)C)([CH3:32])[CH3:31]>O1CCCC1>[CH3:27][O:28][CH2:29][O:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([CH:14]([CH2:31][CH2:30][CH3:32])[C:15]([O:17][CH3:18])=[O:16])=[C:12]([CH3:19])[N:11]=[C:10]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 83093Bromomethyl methyl etherHCID 66956119HCID 66956119, compound

Product 1

HCID 66955906HCID 66955906, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(4-(3-hydroxyphenyl)-6-methyl-2-phenylpyrimidin-5-yl)acetate (150 mg; 0.449 mmol), bromo(methoxy)methane (73.3 μL; 0.897 mmol) and N,N-Diisopropylethylamine (116 μL; 0.673 mmol) were added to a flask at room temperature, dissolved in tetrahydrofuran (449 μL) and heated to reflux for 1 h. The reaction mixture was cooled to room temperature. The salts were removed by filtration and the filtrate was washed with water, brine, dried over magnesium sulphate and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (10-80%) in heptane to give 86 mg (49%) of the title compound as a colorless oil. ESI/APCI(+): 378 (M+H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. customThe salts were removed by filtration
  4. washthe filtrate was washed with water, brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (10-80%) in heptane

Sources & evidence

ORD record
ord-0f654cb86ddf48fca0c9178123fbebbf
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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