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Dimethylformamide → 8-Chloroimidazo[1,5-a]pyrazine

HRID 448985
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HRID 448985 반응식
[Cl:1][C:2]1[C:3]([CH2:8][NH:9][CH:10]=O)=[N:4][CH:5]=[CH:6][N:7]=1.CC#N.O=P(Cl)(Cl)Cl.CN(C=O)C>O>[Cl:1][C:2]1[C:3]2[N:4]([CH:10]=[N:9][CH:8]=2)[CH:5]=[CH:6][N:7]=1
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참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 58902031HCID 58902031, 화합물

생성물 1

HCID 122404758-Chloroimidazo[1,5-a]pyrazine

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To an oven dried flask filled with nitrogen was added N-(3-chloro-pyrazin-2-ylmethyl)-formamide (3.000 g, 0.01748 mol) followed by MeCN (60 mL). POCl3 (4.89 mL, 0.0524 mol) was added to the reaction mixture dropwise at 0° C. and the reaction mixture was stirred at 0° C. for 5 min before DMF (0.2 mL) was added. The mixture was then warmed up to rt and stirred at rt for overnight. The excess of POCl3 was removed under reduced pressure and the residue was quenched with solution of 2N NH3 in i-PrOH at 0° C. with vigorous stirring to adjust the pH to 9. The crude reaction mixture was then charged with water and the aqueous layer was washed with DCM. The combined organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the titled compound. 1H NMR (400 MHz, CDCl3) δ 7.38 (d, J=4.80 Hz, 1H) 7.80 (d, J=5.05 Hz, 1H) 7.87 (s, 1H) 8.28 (s, 1H). MS (ES+): m/z 154.13, 156.02 [MH+]; HPLC: tR=2.02 min (OpenLynx, polar—7 min).

후처리

  1. customTo an oven dried flask
  2. additionfilled with nitrogen
  3. additionwas added
  4. customThe excess of POCl3 was removed under reduced pressure
  5. customthe residue was quenched with solution of 2N NH3 in i-PrOH at 0° C.
  6. stirringwith vigorous stirring
  7. customThe crude reaction mixture
  8. washthe aqueous layer was washed with DCM
  9. dry with materialThe combined organic layer was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-43eebe2beb074cb194368922b83a79d0
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08481733B2

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