Hydrochloric Acid → 4-{2-[(2-Aminoethyl)amino]-5-imidazolylpyrimidin-4-yl}benzenecarbonitrile

HRID 1823433Notes

Reaction equation

HRID 1823433 reaction equation
Cl.C(OC([NH:9][CH2:10][CH2:11][NH:12][C:13]1[N:18]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=2)[C:16]([C:27]2[NH:28][CH:29]=[CH:30][N:31]=2)=[CH:15][N:14]=1)=O)(C)(C)C>CC#N>[NH2:9][CH2:10][CH2:11][NH:12][C:13]1[N:18]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=2)[C:16]([C:27]2[NH:31][CH:30]=[CH:29][N:28]=2)=[CH:15][N:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131723668(Tert-butoxy)-n-(2-{[4-(4-cyanophenyl)-5-imidazolylpyrimidin-2-yl]amino}ethyl)carboxamide

Product 1

HCID 572319134-{2-[(2-Aminoethyl)amino]-5-imidazolylpyrimidin-4-yl}benzenecarbonitrileYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Aqueous 3M HCl (15-30 ml) was added to a stirred solution of (tert-butoxy)-N-(2-{[4-(4-cyanophenyl)-5-imidazolylpyrimidin-2-yl]amino}ethyl)carboxamide (0.15 M) in CH3CN (50 ml) at room temperature until the reaction became slightly turbid. After 16 hours, the reaction was partitioned between dichloromethane (200 ml) and 1M HCl (200 ml). The layers were separated, and the aqueous layer was extracted with dichloromethane (3×200 ml). The aqueous layer was basified carefully with solid NaHCO3 to pH 7-8. A solid forms which can be filtered and dissolved in CH3CN (100 ml). The organic solution is washed with sat. aq. NaHCO3 (50 ml), brine (50 ml), dried with Na2SO4, filtered, and concentrated. The crude product was purified by flash chromatography over silica gel. The column was eluted first with a 1:1 mixture of dichloromethane/methanol followed by a mixture of 5% TEA/10% water/85% methanol to elute the product. The proper fractions were condensed. The dark yellow glass was dried overnight in vacuo giving 4-{2-[(2-aminoethyl)amino]-5-imidazolylpyrimidin-4-yl}benzenecarbonitrile in 89% yield.

Workup

  1. customthe reaction was partitioned between dichloromethane (200 ml) and 1M HCl (200 ml)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with dichloromethane (3×200 ml)
  4. filtrationA solid forms which can be filtered
  5. dissolutiondissolved in CH3CN (100 ml)
  6. washThe organic solution is washed with sat. aq. NaHCO3 (50 ml), brine (50 ml)
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by flash chromatography over silica gel
  11. washThe column was eluted first with a 1:1 mixture of dichloromethane/methanol
  12. additionfollowed by a mixture of 5% TEA/10% water/85% methanol
  13. washto elute the product
  14. customcondensed
  15. customThe dark yellow glass was dried overnight in vacuo

Sources & evidence

ORD record
ord-a8425ece9d7e4699b45d3d18fa6d2dd3
Source dataset
uspto-grants-2006_05
Patent number
US07037918B2

Reaction notes

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