Methanol → 4-chloro-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 988822ノート

反応式

HRID 988822 の反応式
C1(S([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([Cl:19])[C:13]=3[CH:12]=[C:11]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=O)=O)C=CC=CC=1.CO.[OH-].[Na+]>C1COCC1>[Cl:19][C:18]1[C:13]2[CH:12]=[C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[NH:10][C:14]=2[N:15]=[CH:16][N:17]=1

参加物

5

反応物 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 224845527-Benzenesulfonyl-4-chloro6-phenyl-7H-pyrrolo[2,3-d]pyrimidine

生成物 1

HCID 224844424-chloro-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine収率 76%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The product from Method C was dissolved in 10 mL of THF and to this solution was added 5.0 mL of methanol and 1.0 grams of NaOH. The reaction mixture was stirred for 15 minutes, concentrated in vacuo and partitioned between a saturated aqueous solution of ammonium chloride (NH4Cl) and ethyl acetate. The resulting aqueous layer was extracted twice with ethyl acetate. The ethylacetate layers were combined, washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by silica-gel chromatography (1:5 ethyl-acetate/hexane) to obtain 0.59 grams (76%) of the title compound as a pale yellow solid, mp 145° C. (dec). LRMS: 230, 232 (M+2).

後処理

  1. concentrationconcentrated in vacuo
  2. custompartitioned between a saturated aqueous solution of ammonium chloride (NH4Cl) and ethyl acetate
  3. extractionThe resulting aqueous layer was extracted twice with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica-gel chromatography (1:5 ethyl-acetate/hexane)

出典と根拠

ORDレコード
ord-190a62d020ab4fb092b84635bf2cd574
出典データセット
uspto-grants-2003_10
特許番号
US06635762B1

反応ノート

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