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

HRID 1796097Notes

Reaction equation

HRID 1796097 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-94d7866bf33345228c1099be71754548
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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