Water → 5-[3-Trimethylsilyl-ethynyl-4,5-dimethoxy-benzyl]-pyrimidine-2,4-diamine

HRID 963391노트

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HRID 963391 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16](I)[C:17]=1[O:18][CH3:19])[CH2:6][C:7]1[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=1.C([Si:23]([CH3:26])([CH3:25])[CH3:24])#C.O.[CH2:28](N(CC)CC)[CH3:29]>CN(C)C=O.[Cu]I>[CH3:24][Si:23]([CH3:26])([CH3:25])[C:16]1[CH:15]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:17]=1[O:18][CH3:19])[CH:6]([C:28]#[CH:29])[C:7]1[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 111010945-(3,4-Dimethoxy-5-iodo-benzyl)pyrimidine-2,4-diamine

생성물 1

HCID 190815445-[3-Trimethylsilyl-ethynyl-4,5-dimethoxy-benzyl]-pyrimidine-2,4-diamine수율 59%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 8.7 g of 5-(3,4-dimethoxy-5-iodobenzyl)-pyrimidine-2,4-diamine, 6.2 ml of ethynyltrimethylsilane, 80 mg of bis-trimethylphosphine-palladium dichloride and 1 mg of copper(I) iodide in 25 ml of triethylamine and 25 ml of dimethylformamide is stirred at 60° for 16 hrs. After cooling to room temperature the reaction mixture is treated with 400 ml of water and extracted three times with 200 ml of methylene chloride each time. The combined organic phases are washed twice with 250 ml of water, once with 250 ml of a saturated sodium chloride solution and dried over magnesium sulphate. The crude product is chromatographed on silica gel with methylene chloride/methanol 9:1. 4.73 g (59%) of 5-[3-trimethylsilyl-ethynyl-4,5-dimethoxy-benzyl]-pyrimidine-2,4-diamine are obtained as beige crystals. M.p. 189°-190°.

후처리

  1. extractionextracted three times with 200 ml of methylene chloride each time
  2. washThe combined organic phases are washed twice with 250 ml of water, once with 250 ml of a saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. customThe crude product is chromatographed on silica gel with methylene chloride/methanol 9:1

출처 및 근거

ORD 기록
ord-796060440b9c4307b5154120d4c9930d
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05763450

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