2-{6-[7-(1-Methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidin-3-yl]pyridin-2-yl}benzonitrile → 2-{6-[7-(1-Hydroxy-1-methylethyl)imidazo[1,2-alpha]pyrimidin-3-yl]pyridin-2-yl}benzonitrile

HRID 1796037Notes

Reaction equation

HRID 1796037 reaction equation
[CH3:1][C:2]([C:12]1[CH:17]=[CH:16][N:15]2[C:18]([C:21]3[N:26]=[C:25]([C:27]4[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=4[C:29]#[N:30])[CH:24]=[CH:23][CH:22]=3)=[CH:19][N:20]=[C:14]2[N:13]=1)([O:4][Si](CC)(CC)CC)[CH3:3]>C(O)C.Cl>[OH:4][C:2]([C:12]1[CH:17]=[CH:16][N:15]2[C:18]([C:21]3[N:26]=[C:25]([C:27]4[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=4[C:29]#[N:30])[CH:24]=[CH:23][CH:22]=3)=[CH:19][N:20]=[C:14]2[N:13]=1)([CH3:1])[CH3:3]

Participants

4

Reactant 1

HCID 695602202-{6-[7-(1-Methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidin-3-yl]pyridin-2-yl}benzonitrile

Product 1

HCID 101088622-{6-[7-(1-Hydroxy-1-methylethyl)imidazo[1,2-alpha]pyrimidin-3-yl]pyridin-2-yl}benzonitrile

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

To a solution of crude 2-{6-[7-(1-methyl-1-triethylsilanyloxy-ethyl)imidazo[1,2-α]pyrimidin-3-yl]pyridin-2-yl}benzonitrile in ethanol (3 ml) was added 3 drops of concentrated hydrochloric acid and the mixture left to stir at ambient temperature for 18 h. The solvent was evaporated and the residue made basic by the addition of saturated aqueous sodium hydrogencarbonate. The aqueous phase was diluted with water (30 ml) and extracted with ethyl acetate (2×75 ml). The combined organic phase was washed with water (30 ml) and brine (30 ml), dried over anhydrous sodium sulfate, filtered and evaporated to give an orange oil. This oil was purified on silica eluting with dichloromethane (+1% 0.880 ammonia) on a gradient of methanol (1-3%). Collecting the appropriate fractions followed by recrystallisation from ethyl acetate/isohexane gave 2-{6-[7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyrimidin-3-yl]pyridin-2-yl}benzonitrile as a white solid: δH (360 MHz, CDCl3) 1.63 (6H, s), 4.52 (1H, s), 7.16 (1H, d, J 7), 7.55-7.62 (2H, m), 7.74-7.96 (5H, m), 8.36 (1H, s), 10.37 (1H, d, J 7); m/z (ES+) 356 (M++H).

Workup

  1. waitthe mixture left
  2. customThe solvent was evaporated
  3. additionthe residue made basic by the addition of saturated aqueous sodium hydrogencarbonate
  4. additionThe aqueous phase was diluted with water (30 ml)
  5. extractionextracted with ethyl acetate (2×75 ml)
  6. washThe combined organic phase was washed with water (30 ml) and brine (30 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customto give an orange oil
  11. customThis oil was purified on silica eluting with dichloromethane (+1% 0.880 ammonia) on a gradient of methanol (1-3%)
  12. customCollecting the appropriate fractions
  13. customfollowed by recrystallisation from ethyl acetate/isohexane

Sources & evidence

ORD record
ord-0dd5c9e450054a9d86ec861e7a366ecf
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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