Imidazole → HCID 68422267, compound

HRID 657752Notes

Reaction equation

HRID 657752 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C@@H:9]([OH:12])[CH2:10][OH:11])=[CH:5][N:4]=1.N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].O>C(Cl)Cl>[Si:18]([O:11][CH2:10][C@@H:9]([C:6]1[CH:7]=[N:8][C:3]([O:2][CH3:1])=[N:4][CH:5]=1)[OH:12])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 59840706(1R)-1-(2-Methoxy-5-pyrimidinyl)-1,2-ethanediol

Product 1

HCID 68422267HCID 68422267, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of (R)-1-(2-methoxypyrimidin-5-yl)ethane-1,2-diol (3.46 g, 20.3 mmol) and imidazole (3.08 g, 44.7 mmol) was dissolved in methylene chloride (40 mL). The mixture was cooled to 0° C. and tert-butyldimethylsilyl chloride (3.48 g, 22.4 mmol) dissolved in methylene chloride (40 mL) was added. The reaction was stirred for 30 minutes at 0° C. and then reacted at room temperature overnight. The mixture was treated with water (200 mL) and extracted with methylene chloride (2×200 mL). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by silica gel chromatography (0-50% EtOAc/hexane) to afford a colorless oil.

Workup

  1. additionwas added
  2. customreacted at room temperature overnight
  3. extractionextracted with methylene chloride (2×200 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (0-50% EtOAc/hexane)
  7. customto afford a colorless oil

Sources & evidence

ORD record
ord-d539316ddd884c13870733e0609d7528
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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