Methyl iodide → 6-(4-Methoxydibenzo[b,d]furan-1-yl)-3-methyl-4-oxo-3,4,5,6,7,8-hexahydroquinazoline-6-carbonitrile

HRID 2383982ノート

反応式

HRID 2383982 の反応式
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[C:6]([C:16]2([C:27]#[N:28])[CH2:25][CH2:24][C:23]3[N:22]=[CH:21][NH:20][C:19](=[O:26])[C:18]=3[CH2:17]2)=[CH:5][CH:4]=1.[C:29](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[C:6]([C:16]2([C:27]#[N:28])[CH2:25][CH2:24][C:23]3[N:22]=[CH:21][N:20]([CH3:29])[C:19](=[O:26])[C:18]=3[CH2:17]2)=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 1356204896-(4-Methoxydibenzo[b,d]furan-1-yl)-4-oxo-3,4,5,6,7,8-hexahydroquinazoline-6-carbonitrile

生成物 1

HCID 248044526-(4-Methoxydibenzo[b,d]furan-1-yl)-3-methyl-4-oxo-3,4,5,6,7,8-hexahydroquinazoline-6-carbonitrile収率 52%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a well stirred slurry of compound obtained in example 13 (75 mg, 0.2 mmol) and cesium carbonate (73 mg, 0.22 mmol) in dry DMF (5 ml) was added iodomethane (36.92 mg, 0.26 mol) and the mixture was allowed to stir for 1 hr at room temperature under nitrogen atmosphere. The reaction mixture was quenched with ice water (50 ml), and then extracted with ethyl acetate (50 ml). The organic layer was washed with water followed by brine and dried over sodium sulfate. The organic layer was concentrated under vacuum and the crude product was purified by column chromatography to get 40 mg of the pure product (Yields-52%) MP-235.4-240.8° C.

後処理

  1. customThe reaction mixture was quenched with ice water (50 ml)
  2. extractionextracted with ethyl acetate (50 ml)
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationThe organic layer was concentrated under vacuum
  6. customthe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-33be2c9f1b5749918a0a4c50384c2106
出典データセット
uspto-grants-2012_09
特許番号
US08263648B2

反応ノート

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