Benzyl Alcohol → 2-(Benzyloxy)-N-(2,4-dimethoxybenzyl)pyrimidin-4-amine

HRID 337982

Reaction equation

HRID 337982 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9](F)[N:8]=1.[CH2:20]([OH:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH2:20]([O:27][C:9]1[N:8]=[C:7]([NH:6][CH2:5][C:4]2[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:3]=2[O:2][CH3:1])[CH:12]=[CH:11][N:10]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 89963279N-(2,4-dimethoxybenzyl)-2-fluoropyrimidin-4-amine

Product 1

HCID 899628682-(Benzyloxy)-N-(2,4-dimethoxybenzyl)pyrimidin-4-amineYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the N-(2,4-dimethoxybenzyl)-2-fluoropyrimidin-4-amine (2.50 g, 9.50 mmol) prepared in Example 95a and benzyl alcohol (1.97 mL, 19.0 mmol) in DMF (48 mL), sodium hydride (0.90 g, 23.7 mmol) was added, and the reaction solution was stirred at room temperature for 6 hours. To the reaction solution, an aqueous ammonium chloride solution (200 mL) was added, followed by extraction with ethyl acetate (100 mL). The thus obtained organic layer was washed twice with water (200 mL) and dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (hexane/ethyl acetate=1:2) to yield the title compound (3.29 g, 99%) as a colorless amorphous solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate (100 mL)
  2. washThe thus obtained organic layer was washed twice with water (200 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationAfter vacuum concentration
  5. customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=1:2)

Sources & evidence

ORD record
ord-7b3ea41c23bc417593694accaf015a27
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Linked notes

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