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

HRID 2054355노트

반응식

HRID 2054355 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-41b154386de7434eb6dedd2a7d7a4aec
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07329666B2

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