Imidazole → HCID 67257102, compound

HRID 1845871Notes

Reaction equation

HRID 1845871 reaction equation
CC1(C)[O:6][CH:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[N:8]=2)[CH2:4][O:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=CN=C1.[Si:32](Cl)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]>CO.CN(C)C=O>[NH2:13][C:9]1[N:8]=[C:7]([CH:5]([OH:6])[CH2:4][O:3][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH:12]=[CH:11][N:10]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 521998p-Toluenesulfonic acid monohydrateHCID 67256546HCID 67256546, compound

Product 1

HCID 67257102HCID 67257102, compoundYield 8.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2,2-dimethyl-1,3-dioxolan-4-yl)pyrimidin-2-amine (2f) (7.18 g) in methanol (300 mL) was added p-toluenesulfonic acid monohydrate (10.49 g) and the solution was stirred at room temperature overnight. The mixture was filtered through sodium carbonate and concentrated under vacuum to give a brown solid that was dissolved in N,N-dimethylformamide (400 mL) to which was added imidazole (5.2 g) and tert-butyldimethylsilyl chloride (7.7 g) and the solution was stirred at room temperature overnight. The mixture was concentrated on silica under vacuum and purified by silica flash chromatography eluting with 50% to 75% ethyl acetate in heptane to give the title compound (850 mg).

Workup

  1. filtrationThe mixture was filtered through sodium carbonate
  2. concentrationconcentrated under vacuum
  3. customto give a brown solid that
  4. stirringthe solution was stirred at room temperature overnight
  5. concentrationThe mixture was concentrated on silica under vacuum
  6. custompurified by silica flash chromatography
  7. washeluting with 50% to 75% ethyl acetate in heptane

Sources & evidence

ORD record
ord-63124ca53e4947948c870c0874eeb8d5
Source dataset
uspto-grants-2015_02
Patent number
US08952001B2

Reaction notes

Loading…