Tributylvinyltin → methyl 3-[4-[(2,4-difluorobenzyl)oxy]-6-oxo-5-vinylpyrimidin-1(6H)-yl]-4-methylbenzoate

HRID 350936노트

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HRID 350936 반응식
[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[CH2:4][O:5][C:6]1[N:7]=[CH:8][N:9]([C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=2[CH3:24])[C:17]([O:19][CH3:20])=[O:18])[C:10](=[O:13])[C:11]=1I.[CH2:30]([Sn](CCCC)(CCCC)C=C)[CH2:31]CC.[Sn]>CN(C)C=O.[Pd]>[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[CH2:4][O:5][C:6]1[N:7]=[CH:8][N:9]([C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=2[CH3:24])[C:17]([O:19][CH3:20])=[O:18])[C:10](=[O:13])[C:11]=1[CH:30]=[CH2:31]

참가 물질

6

반응물 3

HCID 81998TributylvinyltinHCID 5352426Tin atomHCID 21089020methyl 3-[4-[(2,4-difluorobenzyl)oxy]-5-iodo-6-oxopyrimidin-1(6H)-yl]-4-methylbenzoate

생성물 1

HCID 21090187methyl 3-[4-[(2,4-difluorobenzyl)oxy]-6-oxo-5-vinylpyrimidin-1(6H)-yl]-4-methylbenzoate

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

A round bottom flask containing methyl 3-[4-[(2,4-difluorobenzyl)oxy]-5-iodo-6-oxopyrimidin-1(6H)-yl]-4-methylbenzoate (2.50 g, 4.88 mmol) in N, N-dimethylformamide was evacuated and flushed with argon. Tributyl(vinyl)tin (2.3 g, 7.3 mmol) and dichlorobis(triphenylphosphine) palladium (II) (0.34 g, 0.49 mmol) were added in the nitrogen atmosphere of a glove box. Heated at 60° C. under argon overnight. Added additional tin (0.7 mL) and palladium (0.17 g) reagents and continued over weekend. No progress observed. Distilled DMF, washed crude product with ethyl acetate, and filtered through celite. The filtrate was concentrated and purified by flash column using 25% ethyl acetate in hexane as eluent. Used without further purification.

후처리

  1. customwas evacuated
  2. customflushed with argon
  3. waitcontinued over weekend
  4. washDistilled DMF, washed crude product with ethyl acetate
  5. filtrationfiltered through celite
  6. concentrationThe filtrate was concentrated
  7. custompurified by flash column
  8. customUsed without further purification

출처 및 근거

ORD 기록
ord-ed446d75674849aa989e0813bb7bfe65
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183287B2

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