Imidazole → HCID 86618720, compound

HRID 447631Notes

Reaction equation

HRID 447631 reaction equation
[I:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]2[C@@H:13]3[O:14][C:15]([CH3:18])([CH3:17])[O:16][C@@H:12]3[C@@H:11]([CH2:19][OH:20])[CH2:10]2)[CH:3]=1.N1C=CN=C1.[Si:26](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>CN(C=O)C.O>[Si:26]([O:20][CH2:19][C@@H:11]1[C@H:12]2[O:16][C:15]([CH3:17])([CH3:18])[O:14][C@H:13]2[C@H:9]([NH:8][C:4]2[CH:3]=[C:2]([I:1])[N:7]=[CH:6][N:5]=2)[CH2:10]1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 86618721HCID 86618721, compound

Product 1

HCID 86618720HCID 86618720, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of {(3aR,4R,6R,6aS)-6-[(6-iodopyrimidin-4-yl)amino]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}methanol (1.321 g, 3.38 mmol) and 1H-imidazole (0.552 g, 8.10 mmol) in DMF (16.9 mL) was added tert-butyldimethylsilyl chloride (0.534 g, 3.54 mmol) and the reaction was stirred overnight. The solution was diluted with H2O and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude mixture was purified by flash chromatography (10 to 40% EtOAc/hexanes) to afford the title compound (1.465 g, 86%). LC/MS: Rt=2.47 min ES+ 506 (FA Standard).

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude mixture was purified by flash chromatography (10 to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-aac7537f11fe48e5854ad0372c977af3
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Reaction notes

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