Sodium Bicarbonate → 1-[3-(2-(Pyridin-4-yl)pyrimidin-4-yl)imidazo[1,2-alpha]pyrimidin-7-yl]ethanone

HRID 1796097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1796097
C[O:2][C:3]([C:7]1[CH:12]=[CH:11][N:10]2[C:13]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]4[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=4)[N:17]=3)=[CH:14][N:15]=[C:9]2[N:8]=1)(OC)[CH3:4].CO.C(Cl)Cl.C([O-])(O)=O.[Na+]>Cl>[N:25]1[CH:24]=[CH:23][C:22]([C:18]2[N:17]=[C:16]([C:13]3[N:10]4[CH:11]=[CH:12][C:7]([C:3](=[O:2])[CH3:4])=[N:8][C:9]4=[N:15][CH:14]=3)[CH:21]=[CH:20][N:19]=2)=[CH:27][CH:26]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 102921157-(1,1-Dimethoxyethyl)-3-[2-(pyridin-4-yl)pyrimidin-4-yl]imidazo[1,2-alpha]pyrimidineHCID 21226129Dichloromethane methanol

Produkt 1

HCID 99229231-[3-(2-(Pyridin-4-yl)pyrimidin-4-yl)imidazo[1,2-alpha]pyrimidin-7-yl]ethanoneAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

A solution of 7-(1,1-dimethoxyethyl)-3-[2-(pyridin-4yl)pyrimidin-4-yl]imidazo[1,2-α]pyrimidine (Example 60) (3 g, 8.3 mmol) in 2.5N HCl (60 ml) was heated at 50° C. for 4 h. To the cooled solution was added 5% MeOH/DCM (500 ml) then neutralized by portionwise addition of a saturated solution of NaHCO3. Organic layer was separated and the aqueous re-extracted twice with 5% MeOH/DCM. Combined organics washed with brine, dried (MgSO4) and concentrated in vacuo to give the crude residue. The crude was purified using 100 g silica bond elute cartridge, eluting with 1-2.5% MeOH/DCM, to afford 1-[3-(2-(pyridin-4-yl)pyrimidin-4-yl)imidazo[1,2-α]pyrimidin-7-yl]ethanone as a yellow solid (1.6 g, 61%): 1H NMR (400 MHz, d6DMSO) δ 2.74 (3H, s), 7.92 (1H, d, J 7.2), 8.23 (1H, d, J 5.5), 8.37 (2H, dd, J 1.6, 4.3), 8.83 (2H, dd, J 1.6, 4.3), 9.04 (1H, d, J 5.5), 9.15 (1H, s), 10.39 (1H, d, J 7.4); m/z (ES+) 317 (M+H+).

Aufarbeitung

  1. customOrganic layer was separated
  2. extractionthe aqueous re-extracted twice with 5% MeOH/DCM
  3. washCombined organics washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give the crude residue
  7. customThe crude was purified
  8. washelute cartridge
  9. washeluting with 1-2.5% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-94d7866bf33345228c1099be71754548
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07030128B2

Notizen zur Reaktion

Wird geladen…