Water → methyl 1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

HRID 1766172

反応式

HRID 1766172 の反応式
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]1.Cl[C:15]1[C:16]2[CH:23]=[CH:22][N:21]([CH3:24])[C:17]=2[N:18]=[CH:19][N:20]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.C(OCC)(=O)C>[CH3:24][N:21]1[C:17]2[N:18]=[CH:19][N:20]=[C:15]([N:1]3[C:5]4=[N:6][CH:7]=[CH:8][CH:9]=[C:4]4[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]3)[C:16]=2[CH:23]=[CH:22]1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2658294-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidineHCID 21110084methyl 1H-pyrrolo[2,3-b]pyridine-3-carboxylate

生成物 1

HCID 21110083methyl 1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate収率 44.2%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

To 1.9 g (9.2 mmol) of methyl 1H-pyrrolo[2,3-b]pyridine-3-carboxylate in 50 cm3 of dimethylsulfoxyde under argon atmosphere, were added 1.85 g (11.0 mmol) of 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, followed by 3.2 g (23.0 mmol) of potassium carbonate. The reaction mixture was heated at about 120° C. for 24 hours, upon which it was cooled to about 20° C. and treated with 200 cm3 of distilled water. The mixture was then treated with 300 cm3 and 150 cm3 of ethyl acetate and filtered on Celite®. The aqueous phase was extracted with 150 cm3 of ethyl acetate. The combined organic extracts were dried on magnesium sulfate and concentrated to dryness in vacuo (2.7 kPa). The residue was purified via column chromatography on silica gel (0,04–0,06 mm), with dichloromethane/methanol 99:1 v/v as eluting solvent. Thus, 1.25 g of methyl 1-(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate were obtained as a light-yellow crystalline powder. mp: 207° C.

後処理

  1. temperaturewas cooled to about 20° C.
  2. filtrationfiltered on Celite®
  3. extractionThe aqueous phase was extracted with 150 cm3 of ethyl acetate
  4. customThe combined organic extracts were dried on magnesium sulfate
  5. concentrationconcentrated to dryness in vacuo (2.7 kPa)
  6. customThe residue was purified via column chromatography on silica gel (0,04–0,06 mm), with dichloromethane/methanol 99:1 v/v
  7. washas eluting solvent

出典と根拠

ORDレコード
ord-f419793e4f1b472aad89c56087eeb7fa
出典データセット
uspto-grants-2007_06
特許番号
US07230007B2

関連ノート

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