2-Aminopyrimidine → 2-Methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine

HRID 241432

반응식

HRID 241432 반응식
Br[CH:2]([CH3:15])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)=O.[NH2:16][C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1.C(=O)(O)[O-].[Na+]>CC(O)C>[CH3:15][C:2]1[N:16]=[C:17]2[N:22]=[CH:21][CH:20]=[CH:19][N:18]2[C:3]=1[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1

참가 물질

5

반응물 3

HCID 79782-AminopyrimidineHCID 516892Sodium BicarbonateHCID 104238192-Bromo-1-(4-(trifluoromethyl)phenyl)propan-1-one

생성물 1

HCID 710597752-Methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

In a thermally controlled reactor, stir a mixture of 2-bromo-1-[4-(trifluoromethyl)phenyl]propan-1-one (500 g, 1.78 mol, 1 equiv), IPA (5 L), 2-aminopyrimidine (205 g, 2.13 mol, 1.2 equiv), and sodium bicarbonate (298.8 g, 3.55 mol, 2 equiv) at 80° C. for 18 hours. Cool the suspension, and concentrate in vacuo. Dilute the resulting mixture in DCM (5 L), and wash with brine (2 L). Re-extract the brine wash with DCM (2.5 L); combine all the organic phases; and dry over MgSO4; filter; and collect the filtrate. Concentrate the filtrate to dryness under reduced pressure, and slurry the resulting red gum in Et2O (1.5 L). Collect the resulting solid by filtrate, and air dry for 45 min to give the title compound as a fine, off white solid (108 g, 22% yield). MS (m/z) 278 (M+1).

후처리

  1. temperatureCool the suspension
  2. concentrationconcentrate in vacuo
  3. additionDilute the resulting mixture in DCM (5 L)
  4. washwash with brine (2 L)
  5. washRe-extract the brine wash with DCM (2.5 L)
  6. dry with materialand dry over MgSO4
  7. filtrationfilter
  8. customand collect the filtrate
  9. concentrationConcentrate the filtrate to dryness under reduced pressure
  10. customCollect the resulting solid by filtrate, and air
  11. customdry for 45 min

출처 및 근거

ORD 기록
ord-705882bb16214e3b947072f0284455fb
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648200B2

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