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

HRID 1796097ノート

反応式

HRID 1796097 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-94d7866bf33345228c1099be71754548
出典データセット
uspto-grants-2006_04
特許番号
US07030128B2

反応ノート

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