2,4-dichloro-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine → 2,4-Dichloro-5-methyl-7-tosyl-7h-pyrrolo[2,3-d]pyrimidine

HRID 1014559노트

반응식

HRID 1014559 반응식
[Cl:1][C:2]1[N:3]=[C:4]([Cl:22])[C:5]2[C:10](I)=[CH:9][N:8]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]=2[N:7]=1.[Cl-].[CH3:24][Zn+]>C1COCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([Cl:22])[C:5]2[C:10]([CH3:24])=[CH:9][N:8]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]=2[N:7]=1

참가 물질

6

반응물 2

HCID 579902932,4-dichloro-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidineHCID 178477797HCID 178477797, 화합물

생성물 1

HCID 582908522,4-Dichloro-5-methyl-7-tosyl-7h-pyrrolo[2,3-d]pyrimidine

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

2,4-dichloro-5-iodo-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (800 mg, 1.71 mmol) and Pd(PPh3)4 (40 mg, 0.034 mmol) were combined in dry THF (20 ml) and a 2M solution of methylzinc chloride in THF (1.28 ml, 2.56 mmol) was added under N2. The reaction mixture was let stir at 60° C. for 18 h at which time the reaction was diluted with ethyl acetate and the organic layer was washed with a saturated solution of sodium bicarbonate, water and a saturated brine solution, then dried over sodium sulfate. Solvents were removed under reduced pressure and the residue purified by chromatography on SiO2 to afford 2,4-dichloro-5-methyl-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (487 mg, 1.37 mmol) as a tan solid. This reaction was repeated to synthesize sufficient material as needed for subsequent reactions. ESIMS(M+H)+=357.

후처리

  1. washthe organic layer was washed with a saturated solution of sodium bicarbonate, water
  2. dry with materiala saturated brine solution, then dried over sodium sulfate
  3. customSolvents were removed under reduced pressure
  4. customthe residue purified by chromatography on SiO2

출처 및 근거

ORD 기록
ord-f7f39c81dd5e4373b03ba280fdff0867
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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