Carbon Dioxide → 1-(2-Phenylpyrimidin-5-yl)ethanone

HRID 42287

반응식

HRID 42287 반응식
CON(C)[C:4]([C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][CH:11]=1)=[O:5].[C:19](=O)=O.C[Mg]Cl.[Cl-].[NH4+]>C1COCC1.C(OCC)C.C(O)C>[C:12]1([C:9]2[N:10]=[CH:11][C:6]([C:4](=[O:5])[CH3:19])=[CH:7][N:8]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

8

반응물 4

HCID 280Carbon DioxideHCID 25517Ammonium ChlorideHCID 47401292N-methoxy-N-methyl-2-phenylpyrimidine-5-carboxamideHCID 178418332HCID 178418332, 화합물

생성물 1

HCID 226310721-(2-Phenylpyrimidin-5-yl)ethanone수율 78%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-60 °C

실험 절차

A solution consisting of N-methoxy-N-methyl-2-phenylpyrimidine-5-carboxamide (Step I, 1.80 g, 7.39 mmol) in anhydrous THF (20 mL) was cooled in a −60° C. bath (ethanol, CO2(s)). Methylmagnesium chloride (Aldrich, 3.0 M in THF, 2.75 mL, 8.14 mmol) was subsequently added dropwise to the reaction mixture. The reaction mixture was stirred for 30 minutes in the −60° C. bath and was subsequently allowed to warm to room temperature over one hour. The crude reaction mixture was then poured into a separatory funnel that contained diethyl ether (200 mL) and saturated ammonium chloride (150 mL). The organic layer was separated and the aqueous layer was washed again with diethyl ether (100 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford a white solid as the crude product. The crude solid was triturated with a hexane-ethyl acetate (9:1 v/v) mixture (20 mL). The precipitate in solution was filtered to afford the title compound as a white solid (1.15 g, 78% yield); Rf 0.72 with 1:1 v/v hexanes-ethyl acetate; 1H-NMR (400 MHz; CDCl3) δ 9.25 (s, 2H), 8.53 (dd, 2H), 7.58 (m, 3H), 2.63 (s, 3H); MS (APCI+) m/z 199.0 (M+1).

후처리

  1. temperatureto warm to room temperature over one hour
  2. customThe crude reaction mixture
  3. additionwas then poured into a separatory funnel that
  4. customThe organic layer was separated
  5. washthe aqueous layer was washed again with diethyl ether (100 mL)
  6. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto afford a white solid as the crude product
  10. customThe crude solid was triturated with a hexane-ethyl acetate (9:1 v/v) mixture (20 mL)
  11. filtrationThe precipitate in solution was filtered

출처 및 근거

ORD 기록
ord-09b51270ec5243579846fbc0216bf398
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536185B2

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