Chloroform → 4-Methoxy-9-Tosylaminopyrido[3',2':4,5]Pyrrolo[1,2-c]Pyrimidine

HRID 2054361ノート

反応式

HRID 2054361 の反応式
I[C:2]1[C:3]2[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[N:22][C:4]=2[N:5]2[C:10]=1[CH:9]=[CH:8][N:7]=[C:6]2[NH:11][S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13].[SnH3]C1N=CC=CN=1.C(Cl)(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Li+].[Cl-]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Cu]I>[CH3:27][O:26][C:25]1[C:3]2[CH:2]=[C:10]3[CH:9]=[CH:8][N:7]=[C:6]([NH:11][S:12]([C:15]4[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=4)(=[O:14])=[O:13])[N:5]3[C:4]=2[N:22]=[CH:23][CH:24]=1

参加物

9

反応物 5

HCID 6212ChloroformHCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 114433055Iodo-4-Methoxy-9-Tosylaminopyrido[3',2':4,5]Pyrrolo[1,2-c]PyrimidineHCID 871506562-Stannyl pyrimidine

生成物 1

HCID 596557694-Methoxy-9-Tosylaminopyrido[3',2':4,5]Pyrrolo[1,2-c]Pyrimidine収率 29.9%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of 24b (295 mg, 0.60 mmol), 27 (258 mg, 0.9 mmol), Pd2(dba)3.CHCl3 (120 mg, 0.12 mmol), PPh3 (60 mg, 0.24 mmol), LiCl (74 mg, 1.8 mmol) and CuI (23 mg, 0.12 mmol) in dioxane (25 mL) was refluxed for one hour. The solvent was evaporated and the crude dissolved in CH2Cl2. The organic solution was extracted three times with 4N HCl solution. The aqueous solutions were basified together with solid NaHCO3 and extracted with CH2Cl2. The organic solution was evaporated and the mixture was purified by flash column chromatography. Elution with CH2Cl2/MeOH (99/1) gave 23b (66 mg, 28%) and with CH2Cl2/MeOH (9/1) gave 25 (209 mg, 71%) as a yellow solid.

後処理

  1. customThe solvent was evaporated
  2. dissolutionthe crude dissolved in CH2Cl2
  3. extractionThe organic solution was extracted three times with 4N HCl solution
  4. extractionextracted with CH2Cl2
  5. customThe organic solution was evaporated
  6. customthe mixture was purified by flash column chromatography
  7. washElution with CH2Cl2/MeOH (99/1)

出典と根拠

ORDレコード
ord-3e5ff65489a640578fdb71fd89672375
出典データセット
uspto-grants-2008_02
特許番号
US07329666B2

反応ノート

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