4-tert-Butylbenzyl alcohol → 4-(4-t-Butylbenzyloxy)-5-methoxypyrimidine

HRID 339929

Reaction equation

HRID 339929 reaction equation
Cl[C:2]1[C:7]([O:8][CH3:9])=[CH:6][N:5]=[CH:4][N:3]=1.[C:10]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18][OH:19])=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11].[H-].[Na+]>CC(N(C)C)=O>[C:10]([C:14]1[CH:15]=[CH:16][C:17]([CH2:18][O:19][C:2]2[C:7]([O:8][CH3:9])=[CH:6][N:5]=[CH:4][N:3]=2)=[CH:20][CH:21]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 134164-tert-Butylbenzyl alcoholHCID 24758Sodium hydrideHCID 110080394-Chloro-5-methoxypyrimidine

Product 1

HCID 768532354-(4-t-Butylbenzyloxy)-5-methoxypyrimidineYield 77%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 4-chloro-5-methoxypyrimidine (1.5 g, 10.3 mmol) described in Journal of the Chemical Society (1960), 4590, and 4-t-butylbenzylalcohol (2.55 g, 15.6 mmol) in dimethylacetamide (10 mL) was added sodium hydride (0.625 g, 15.6 mmol) at 0° C., and the mixture was stirred at room temperature for 3 hrs. The reaction mixture was poured into ice water, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 4-(4-t-butylbenzyloxy)-5-methoxypyrimidine (2.16 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationthe solvent was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-93733c3d90984d0eb0ecac29f21d3b54
Source dataset
uspto-grants-2014_11
Patent number
US08895574B2

Linked notes

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