Ethyl Acetate → (2-Anilinopyrimidin-5-yl)methanol

HRID 1890660Notes

Reaction equation

HRID 1890660 reaction equation
[C:1]1([NH:7][C:8]2[N:13]=[CH:12][C:11]([C:14](OCC)=[O:15])=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[OH:15][CH2:14][C:11]1[CH:10]=[N:9][C:8]([NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:13][CH:12]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 23156191HCID 23156191, compoundHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 23156172(2-Anilinopyrimidin-5-yl)methanolYield 79.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

Ethyl 2-(phenylamino)pyrimidine-5-carboxylate (0.590 g, 2.42 mmol) obtained in Step 2 was dissolved in toluene (25 mL). After cooling to −78° C., a 1 mol/L diisobutyl aluminum hydride-toluene solution (7.30 mL, 7.30 mmol) was added to the solution, followed by stirring at −78° C. for 3 hours. The reaction mixture was added with ethyl acetate followed by stirring vigorously at room temperature. The mixture was sequentially washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=50:1) to obtain 5-hydroxymethyl-2-(phenylamino)pyrimidine (386 mg, 79%).

Workup

  1. stirringby stirring vigorously at room temperature
  2. washThe mixture was sequentially washed with water and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-a77ae37e2c544395ab70684d61b6495e
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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