Dimethylformamide → 8-Chloro-3-(methylsulfanyl)imidazo[1,5-A]pyrazine

HRID 1992425ノート

反応式

HRID 1992425 の反応式
[CH3:1][S:2][C:3](=O)[NH:4][CH2:5][C:6]1[C:11]([Cl:12])=[N:10][CH:9]=[CH:8][N:7]=1.CN(C=O)C.O=P(Cl)(Cl)Cl>CC#N>[Cl:12][C:11]1[C:6]2[N:7]([C:3]([S:2][CH3:1])=[N:4][CH:5]=2)[CH:8]=[CH:9][N:10]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 59130384(3-chloro-pyrazin-2-ylmethyl)-thiocarbamic acid S-methyl ester

生成物 1

HCID 591303828-Chloro-3-(methylsulfanyl)imidazo[1,5-A]pyrazine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of (3-chloro-pyrazin-2-ylmethyl)-thiocarbamic acid S-methyl ester (3.05 g, 0.0140 mol) in MeCN (70 mL) were added DMF (4.3 mL, 0.056 mol) and POCl3 (5.2 mL, 0.056 mol) at 0° C. under nitrogen. The reaction mixture was slowly warmed to rt and stirred overnight. The solvent was evaporated under reduced pressure and the residue was cooled at 0° C. and diluted with EtOAc (250 mL), then quenched with sat. aq. NaHCO3 (100 mL). The mixture was washed with brine (50 mL), and dried over anhydrous sodium sulfate. The crude material was purified by silica gel chromatography (Hex:EtOAc=80:20→70:30) to give the title compound as a light-yellow solid; LC-MS (ES, Pos.): 200/202 (3/1) [MH+]; 1H NMR (CDCl3, 400 MHz) δ 2.71 (s, 3H), 7.40 (d, J=5.1 Hz, 1H), 7.74 (dd, J=5.1, 1.0 Hz, 1H), 7.90 (s, 1H).

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. temperaturethe residue was cooled at 0° C.
  3. additiondiluted with EtOAc (250 mL)
  4. customquenched with sat. aq. NaHCO3 (100 mL)
  5. washThe mixture was washed with brine (50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe crude material was purified by silica gel chromatography (Hex:EtOAc=80:20→70:30)

出典と根拠

ORDレコード
ord-e54198d0935245ad969c8dee102cd68f
出典データセット
uspto-grants-2010_01
特許番号
US07648987B2

反応ノート

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