7H-Pyrrolo(2,3-d)pyrimidine, 4-chloro- → 4-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 1690040ノート

反応式

HRID 1690040 の反応式
Cl[C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH:11]1([Mg]Br)[CH2:13][CH2:12]1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(C)C=CC=CC=1>[CH:11]1([C:2]2[C:3]3[CH:10]=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:13][CH2:12]1

参加物

5

反応物 2

HCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 178418630HCID 178418630、化合物

生成物 1

HCID 579633004-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidine収率 99.4%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 1140Toluene溶媒

反応条件

温度
60 °C

実験手順

4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1, 0.452 g, 2.94 mmol), cyclopropylmagnesium bromide (43, 31.4 mL, 0.50 M in tetrahydrofuran, 15.7 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.240 g, complex 1:1 with dichloromethane, 0.294 mmol) were mixed with 15.4 mL of toluene. The reaction was heated at 60° C. overnight, then quenched with 1 M aqueous hydrochoric acid to pH 4 and filtered through a bed of celite. The layers of the filtrate were separated and the aqueous layer extracted with ethyl acetate: The combined organic layers were washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with ethyl acetate and hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (44, 0.465 g). MS (ESI) [M+H+]+=160.1.

後処理

  1. customquenched with 1 M aqueous hydrochoric acid to pH 4
  2. filtrationfiltered through a bed of celite
  3. customThe layers of the filtrate were separated
  4. extractionthe aqueous layer extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under vacuum
  9. customThe resulting material was purified by silica gel column chromatography
  10. washeluting with ethyl acetate and hexane
  11. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-54f04cdc39c34f5baa80dc7d1ace052e
出典データセット
uspto-grants-2012_04
特許番号
US08153641B2

反応ノート

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