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

HRID 1796097노트

반응식

HRID 1796097 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-94d7866bf33345228c1099be71754548
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030128B2

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