HCID 69709578, compound → HCID 9925270, compound

HRID 2183999Notes

Reaction equation

HRID 2183999 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[CH:13]=[CH:14][C:15]([C:17]4([CH3:24])[CH2:21][O:20]C(C)(C)[O:18]4)=[N:16][C:11]3=[N:10][CH:9]=2)=[CH:4][C:3]=1[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1>Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[CH:13]=[CH:14][C:15]([C:17]([OH:18])([CH3:24])[CH2:21][OH:20])=[N:16][C:11]3=[N:10][CH:9]=2)=[CH:4][C:3]=1[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1

Participants

3

Reactant 1

HCID 69709578HCID 69709578, compound

Product 1

HCID 9925270HCID 9925270, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

3-[4-Fluoro-3-(pyridin-3-yl)phenyl]-7-(2,2,4-trimethyl-[1,3]dioxolan-4-yl)imidazo[1,2-α]pyrimidine (1.00 g, 2.47 mmol) was stirred in 2N hydrochloric acid (20 ml) at 70° C. for 10 min. The reaction mixture was allowed to cool and was then loaded onto a strong cation-exchange cartridge. Non-basic impurities were removed by elution with methanol. Elution with 10% ammonia in methanol gave 2-[3-(4-fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propane-1,2-diol as an oil (450 mg) which solidified on standing. Bis-hydrochloride salt (from ethyl acetate/ethanol): δH (360 MHz, d6-DMSO) 1.50 (3H, s), 3.67 (2H, m), 7.74 (1H, dd, J 11 and 8), 7.89 (3H, m), 8.13 (1H, dd, J 7 and 2), 8.51 (1H, d, J 8), 8.58 (1H, s), 8.85 (1H, dd, J 5 and 1), 9.12 (1H, s), 9.40 (1H, d, J 7).

Workup

  1. temperatureto cool
  2. customNon-basic impurities were removed by elution with methanol
  3. washElution with 10% ammonia in methanol

Sources & evidence

ORD record
ord-a47ff026fdfa48059b931a42d141d4da
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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