Methyl Methanesulfonate → 2,4-dichloro-5-methyl-5H-pyrrolo(3,2-d)pyrimidine

HRID 334112

反応式

HRID 334112 の反応式
[Cl:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]2[NH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:12]OS(C)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]2[N:10]([CH3:12])[CH:9]=[CH:8][C:6]=2[N:7]=1

参加物

6

反応物 3

HCID 4156Methyl MethanesulfonateHCID 10796Cesium carbonateHCID 53750532,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine

生成物 1

HCID 147277632,4-dichloro-5-methyl-5H-pyrrolo(3,2-d)pyrimidine収率 87.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine (2.67 g, 14.2 mmol), methanesulfonic acid methyl ester (1.26 mL, 14.9 mmol) and cesium carbonate (9.25 g, 28.4 mmol) in anhydrous N,N-dimethylformamide (21 mL) was stirred at RT (room temperature) under N2 for 15 h. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with 1:1 water/brine (3×) and brine (1×), dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography to give 2.50 g (87.1%) of 2,4-dichloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine as a white solid. MS(ESI) m/z: 202.2/204.1 [M+1]+.

後処理

  1. washthe organic layer was washed with 1:1 water/brine (3×) and brine (1×)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-ad4ab2b30ba54eb98fe767b36759613a
出典データセット
uspto-grants-2014_11
特許番号
US08883799B2

関連ノート

読み込み中…