Benzyl Alcohol → HCID 19977712, compound

HRID 1449441Notes

Reaction equation

HRID 1449441 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:10]1[N:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([O:18][CH3:19])[N:11]=1.[H-].[Na+]>CN(C)C=O.CCCCCC>[CH3:19][O:18][C:12]1[CH:13]=[C:14]([O:16][CH3:17])[N:15]=[C:10]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:11]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 51523232-Chloro-4,6-dimethoxypyrimidine

Product 1

HCID 19977712HCID 19977712, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

Benzyl alcohol (Compound II-64) (0.434 g, 4.0 mmol) and 2-chloro-4,6-dimethoxypyrimidine were dissolved in dimethylformamide (10 ml) and cooled with ice. Sodium hydride (168 mg, 4.0×1.05 mmol) which had been washed with hexane (1 ml×2) was added thereto. After allowed to react for 2 hours, the reaction solution was poured onto ice and extracted with toluene. The organic phase was concentrated and thereafter purified on silica gel column chromatography (Wakogel C300, 100 ml, ethyl acetate/hexane=30 ml/300 ml) to obtain the compound (I-372).

Workup

  1. temperaturecooled with ice
  2. additionwas added
  3. customto react for 2 hours
  4. additionthe reaction solution was poured onto ice
  5. extractionextracted with toluene
  6. concentrationThe organic phase was concentrated
  7. custompurified on silica gel column chromatography (Wakogel C300, 100 ml, ethyl acetate/hexane=30 ml/300 ml)
  8. customto obtain the compound (I-372)

Sources & evidence

ORD record
ord-e6b4792f8f5d468b8d8ec0ecc5f28085
Source dataset
uspto-grants-1997_02
Patent number
US05599770

Reaction notes

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