Imidazole → HCID 57971146, compound

HRID 602299Notes

Reaction equation

HRID 602299 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1>CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2004934-Pyrimidinemethanol, 2-amino-

Product 1

HCID 57971146HCID 57971146, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-4-hydroxymethylpyrimidine (750 mg, 6.0 mmol, Reference Compound No. 4-1) and tert-butyldimethylsilyl chloride (990 mg, 6.6 mmol) were suspended in anhydrous N,N-dimethylformamide (8.0 mL), then imidazole (0.90 g, 13 mmol) was added thereto and the mixture was stirred for 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate (50 mL), washed twice with saturated aqueous sodium hydrogencarbonate solution (50 mL), and then washed with brine (50 mL), and dried over anhydrous magnesium sulfate. Then the solvent was evaporated under reduced pressure, the precipitated solid was filtered off with 50% ethyl acetate-n-hexane solution, and dried under reduced pressure to give 1.2 g of the title Reference Compound as a white solid (Yield: 84%).

Workup

  1. washwashed twice with saturated aqueous sodium hydrogencarbonate solution (50 mL)
  2. washwashed with brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThen the solvent was evaporated under reduced pressure
  5. filtrationthe precipitated solid was filtered off with 50% ethyl acetate-n-hexane solution
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-87875121890441f6ae86c388680edf18
Source dataset
uspto-grants-2011_03
Patent number
US07906511B2

Reaction notes

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