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 1014559ノート

反応式

HRID 1014559 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f7f39c81dd5e4373b03ba280fdff0867
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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