Sodium Hydroxide → 3-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-amine

HRID 456688Notes

Reaction equation

HRID 456688 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[N:17]4[CH:18]=[CH:19][CH:20]=[C:21]([N:22]=CN(C)C)[C:16]4=[N:15][C:14]=3[C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[N:17]4[CH:18]=[CH:19][CH:20]=[C:21]([NH2:22])[C:16]4=[N:15][C:14]=3[C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69549491N'-[3-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-yl]-N,N-dimethylimidoformamide

Product 1

HCID 101783513-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-amineYield 88.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N′-[3-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)imidazo[1,2-α]pyridin-8-yl]-N,N-dimethylimidoformamide (70 mg, 0.16 mmol) was dissoved in methanol. To this solution was added 1N aqueous sodium hydroxide and the resulting mixture heated at reflux for 6 hours. The resulting mixture was concentrated in vacuo followed by addition of ethyl acetate and water. The phases were separated and the ethyl acetate phase dried (magnesium sulfate), filtered and concentrated. The resulting solid was purified by silica gel chromatography (ethyl acetate) to give 55 mg (88%) of 3-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)imidazo[1,2-α]pyridin-8-amine as a solid. 1H NMR (CDCl3): δ 8.97 (d, 1H), 8.12 (d, 1H), 7.68 (q, 2H), 7.15 (t, 2H), 6.78 (t, 1H), 6.54 (d, 1H), 6.41 (d, 1H), 5.24 (d, 1H), 4.60 (s, 2H), 4.40 (m, 1H), 2.0–2.1 (m, 2H), 1.4–1.9 (m, 6H); 19F NMR (CDCl3) δ −113.7; MS m/z 389 (M+1).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 6 hours
  3. concentrationThe resulting mixture was concentrated in vacuo
  4. additionfollowed by addition of ethyl acetate and water
  5. customThe phases were separated
  6. dry with materialthe ethyl acetate phase dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting solid was purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-9923aa4810594f5fa5bf731c8035a638
Source dataset
uspto-grants-2007_03
Patent number
US07186714B2

Reaction notes

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