Triphenylphosphine → 9-Acetylamino-5-(2-methanesulfenylpyrimidin-4-yl)pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine

HRID 2054355ノート

反応式

HRID 2054355 の反応式
[C:1]([NH:4][C:5]1[N:10]2[C:11]3[N:18]=[CH:17][CH:16]=[CH:15][C:12]=3[C:13](I)=[C:9]2[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].[CH3:19][S:20][C:21]1[N:26]=[C:25]([Sn](C)(C)C)[CH:24]=[CH:23][N:22]=1.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>[C:1]([NH:4][C:5]1[N:10]2[C:11]3[N:18]=[CH:17][CH:16]=[CH:15][C:12]=3[C:13]([C:23]3[CH:24]=[CH:25][N:26]=[C:21]([S:20][CH3:19])[N:22]=3)=[C:9]2[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2]

参加物

8

反応物 4

HCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 111523439-Acetylamino-5-Iodopyrido[3',2':4,5]Pyrrolo[1,2-c]PyrimidineHCID 112662292-(Methylthio)-4-(trimethylstannyl)pyrimidine

生成物 1

HCID 99682739-Acetylamino-5-(2-methanesulfenylpyrimidin-4-yl)pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine収率 16.2%

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 20a (130 mg, 0.37 mmol), 2-methanesulfenyl-4-trimethylstannylpyrimidine (93 mg, 1.10 mmol), Pd2(dba)3 (76 mg, 0.07 mmol), PPh3 (39 mg, 0.15 mmol), LiCl (47 mg, 1.10 mmol) and CuI (14 mg, 0.07 mmol) in dioxane (10 ml) was refluxed for 1.5 hours. The organic solvent was removed and the oil dissolved in CH2Cl2. The organic solution was extracted four times with 4N HCl and the aqueous solution basified with solid Na2CO3. The aqueous solution was extracted with CH2Cl2. The organic layer was evaporated and purified by flash column chromatography. Elution with CH2Cl2/MeOH (99/1) gave 9-Acetylamino-5-(2-methanesulfenylpyrimidin-4-yl)pyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidine (21 mg, 16%) as a yellow solid and with CH2Cl2/MeOH (95/5) gave 21 (30 mg, 26%) as a yellow solid.

後処理

  1. customThe organic solvent was removed
  2. dissolutionthe oil dissolved in CH2Cl2
  3. extractionThe organic solution was extracted four times with 4N HCl
  4. extractionThe aqueous solution was extracted with CH2Cl2
  5. customThe organic layer was evaporated
  6. custompurified by flash column chromatography
  7. washElution with CH2Cl2/MeOH (99/1)

出典と根拠

ORDレコード
ord-41b154386de7434eb6dedd2a7d7a4aec
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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