Benzyl Alcohol → HCID 17830651, compound

HRID 2103974Notes

Reaction equation

HRID 2103974 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:12]1[N:17]=[C:16](Cl)[CH:15]=[C:14]([CH3:19])[N:13]=1.[Cl-].[NH4+]>CN(C=O)C>[CH2:3]([O:10][C:12]1[N:17]=[C:16]([O:10][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:15]=[C:14]([CH3:19])[N:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 794712,4-Dichloro-6-methylpyrimidine

Product 1

HCID 17830651HCID 17830651, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of sodium hydride (3.2 g, 80 mmol) in DMF (20 ml) was added under ice-cooling benzylalcohol (8.6 g, 80 mmol). To the solution was added 2,4-dichloro-6-methylpyrimidine (3.2 g, 20 mmol). The mixture was stirred at room temperature for 1 hour. To the reaction mixture was added an aqueous solution of ammonium chloride. The mixture was extracted with diethyl ether, washed with water, dried and concentrated. The obtained residue was chromatographed on silica gel (n-hexane-ethyl acetate). The obtained fraction was concentrated under reduced pressure to give 2,4-bisbenzyloxy-6-methylpyrimidine (3.5 g).

Workup

  1. extractionThe mixture was extracted with diethyl ether
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe obtained residue was chromatographed on silica gel (n-hexane-ethyl acetate)
  6. concentrationThe obtained fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e96f4f37914c4250a164ff74034175ce
Source dataset
uspto-grants-2009_08
Patent number
US07576198B1

Reaction notes

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