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

HRID 988822노트

반응식

HRID 988822 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-190a62d020ab4fb092b84635bf2cd574
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06635762B1

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