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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
ノート
印刷プレビュー

反応式

HRID 2210632 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-7eb8ab37ea6a48dbbbd5efc937a8fb5b
出典データセット
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05459243

反応ノート

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