HCID 69560024, compound → HCID 10292909, compound

HRID 1796095Notes

Reaction equation

HRID 1796095 reaction equation
[CH3:1][C:2]([C:12]1[CH:17]=[CH:16][N:15]2[C:18]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([N+:33]([O-:35])=[O:34])[CH:28]=4)[N:22]=3)=[CH:19][N:20]=[C:14]2[N:13]=1)([O:4][Si](CC)(CC)CC)[CH3:3]>CCO.Cl>[N+:33]([C:29]1[CH:28]=[C:27]([C:23]2[N:22]=[C:21]([C:18]3[N:15]4[CH:16]=[CH:17][C:12]([C:2]([OH:4])([CH3:1])[CH3:3])=[N:13][C:14]4=[N:20][CH:19]=3)[CH:26]=[CH:25][N:24]=2)[CH:32]=[CH:31][CH:30]=1)([O-:35])=[O:34]

Participants

4

Reactant 1

HCID 69560024HCID 69560024, compound

Product 1

HCID 10292909HCID 10292909, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

7-(1-Methyl-1-triethylsilanyloxyethyl)-3-[2-(3-nitrophenyl)-pyrimidin-4-yl]imidazo[1,2-α]pyrimidine in EtOH (10 ml) was treated with conc. HCl (10 drops) and stirred at room temperature for 12 h. The crude mixture was poured onto an SCX cartridge (2 gram) and washed firstly with MeOH (20 ml) to remove the impurities and then 2N NH3 in MeOH (20 ml) to elute the desired compound. Removal of the solvent under reduced pressure afforded 2-{3-[2-(3-nitrophenyl)pyrimidin-4-yl]imidazo[1,2-α]pyrimidin-7-yl}propan-2-ol (66 mg, 28%): 1H NMR (360 MHz, CDCl3) δ 10.31 (1H, d, J 7.3), 9.31 (1H, t, J 1.8), 8.83 (1H, d, J 5.5), 8.80 (1H, d, J 8.0), 8.55 (1H, s), 8.40 (1H, d, J 8.0), 7.75 (1H, t, J 8.0), 7.66 (1H, d, J 5.5), 7.40 (1H, d, J 7.3), 1.68 (6H, s); m/z (ES+) 377 (M+H+).

Workup

  1. washwashed firstly with MeOH (20 ml)
  2. customto remove the impurities
  3. wash2N NH3 in MeOH (20 ml) to elute the desired compound
  4. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-47f0d5b6b5eb4d408b6ae1eda8cbd526
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

Loading…