Benzyl Alcohol → HCID 178494251, compound

HRID 2194785Notes

Reaction equation

HRID 2194785 reaction equation
Cl[C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11][CH3:12])[N:5]=[C:4]([O:13][CH3:14])[N:3]=1.C([OH:22])C1C=CC=CC=1.[H-].[Na+]>CN(C=O)C>[CH:8]([C:7]1[C:2]([OH:22])=[N:3][C:4]([O:13][CH3:14])=[N:5][C:6]=1[O:11][CH3:12])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 160881865-Isopropyl-6-chloro-2,4-dimethoxypyrimidine

Product 1

HCID 178494251HCID 178494251, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 4-chloro-5-isopropyl-2,6-dimethoxy-pyrimidine (1.4 g, 6.51 mmol, 1 eq) and benzyl alcohol (704 mg, 1.0 eq.) in 10 mL DMF, NaH (60% in mineral oil, 273 mg, 1.05 eq.) was added at 0° C. The reaction mixture was stirred at 0° C. then warmed up to room temperature. LC-MS showed that the desired product formed. The reaction mixture was then diluted with ethyl acetate, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give the crude product.

Workup

  1. additionwas added at 0° C
  2. temperaturethen warmed up to room temperature

Sources & evidence

ORD record
ord-3d493567afd54a8dba5cfdc96865353d
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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