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Triethylamine → 4-(1-Hexyn-1-yl)-1-(2-O-methyl-3,5,-di-O-benzoyl-beta-D-ribofuranosyl)pyrimidin-2-one

HRID 2210632
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HRID 2210632 반응식
C(N(CC)CC)C.[CH:8]#[C:9][CH2:10][CH2:11][CH2:12][CH3:13].Cl[C:15]1[CH:20]=[CH:19][N:18]([C@@H:21]2[O:36][C@H:35]([CH2:37][O:38][C:39](=[O:46])[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C@@H:25]([O:26][C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:22]2[O:23][CH3:24])[C:17](=[O:47])[N:16]=1>C1COCC1.[Cu]I>[C:8]([C:15]1[CH:20]=[CH:19][N:18]([C@@H:21]2[O:36][C@H:35]([CH2:37][O:38][C:39](=[O:46])[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C@@H:25]([O:26][C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:22]2[O:23][CH3:24])[C:17](=[O:47])[N:16]=1)#[C:9][CH2:10][CH2:11][CH2:12][CH3:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 127321-HexyneHCID 217824984-Chloro-1-(2-O-methyl-3,5-di-O-benzoyl-beta-D-ribofuranosyl)-pyrimidin-2-one

생성물 1

HCID 228567304-(1-Hexyn-1-yl)-1-(2-O-methyl-3,5,-di-O-benzoyl-beta-D-ribofuranosyl)pyrimidin-2-one

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 8028Tetrahydrofuran용매2회

실험 절차

Bis-triphenylphosphine palladium (II) dichloride (422 mg, 4.3 mmole) and copper (I) iodide (114 mg, 4.3 mmole) were suspended in anhydrous THF (100 ml) and degassed with argon for 10 min. The orange suspension was treated with triethylamine (5 ml) and 1-hexyne (2.96 g, 41 mmole) and stirred for 5 min. A solution of 4-chloro-1-(2-O-methyl-3,5,-di-O-benzoyl-β-D-ribofuranosyl)pyrimidin-2-one (6.74 g, 13.9 mmole) in THF (25 ml) was added all at once. The reaction mixture was stirred for 2 hours at room temperature and evaporated to an oil. The residue was purified by silica gel column chromatography. Elution with chloroform (500 ml) and then chloroform/acetone (98:2, 21), pooling of appropriate fractions and evaporation gave a yield of 3.84 g (52.7%).

후처리

  1. customdegassed with argon for 10 min
  2. stirringThe reaction mixture was stirred for 2 hours at room temperature
  3. customevaporated to an oil
  4. customThe residue was purified by silica gel column chromatography
  5. washElution with chloroform (500 ml)
  6. customchloroform/acetone (98:2, 21), pooling of appropriate fractions and evaporation
  7. customgave a yield of 3.84 g (52.7%)

출처 및 근거

ORD 기록
ord-7eb8ab37ea6a48dbbbd5efc937a8fb5b
출처 데이터셋
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05459243

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