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

HRID 1107649Notes

Reaction equation

HRID 1107649 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].C(N(CC)CC)C.Cl[C:15]1[CH:20]=[CH:19][N:18]([C@@H:21]2[O:43][C@H:42]([CH2:44][O:45][C:46](=[O:53])[C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C@@H:32]([O:33][C:34](=[O:41])[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@H:22]2[O:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:17](=[O:54])[N:16]=1>C1COCC1.[Cu]I>[C:1]([C:15]1[CH:20]=[CH:19][N:18]([C@@H:21]2[O:43][C@H:42]([CH2:44][O:45][C:46](=[O:53])[C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C@@H:32]([O:33][C:34](=[O:41])[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@H:22]2[O:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:17](=[O:54])[N:16]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 127321-HexyneHCID 102575224-Chloro-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)pyrimidin-2-one

Product 1

HCID 103941024-(1-Hexyn-1-yl)-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-pyrimidin-2-one

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of bis-triphenylphosphine palladium (II) dichloride (0.35 g, 0.5 mmol) and copper (I) iodide (95 mg, 0.5 mmol) in THF (45 mL, distilled from Na-benzophenone ketyl) is sparged with dry argon gas for 10 min. To this suspension is added 1-hexyne (2.46 g, 30 mmol) followed by triethylamine (5 mL). The suspension is stirred at room temperature under argon for 15 min. A similarly sparged solution of the 2-chloro-1-(2,3,5-tri-O-benzoyl-b-D-ribofuranosyl)pyrimidin-4-one (13, 5.75 g, 10 mmol) in THF (15 mL) is added to the suspension of catalyst and the mixture stirred for 1 hr. The dark mixture is filtered through Celite and the filtrate evaporated in vacuo to afford a dark syrup. This syrup was triturated with cold diethylether, filtered and then dissolved in dichloromethane.

Workup

  1. customis sparged with dry argon gas for 10 min
  2. stirringthe mixture stirred for 1 hr
  3. filtrationThe dark mixture is filtered through Celite
  4. customthe filtrate evaporated in vacuo
  5. customto afford a dark syrup
  6. customThis syrup was triturated with cold diethylether
  7. filtrationfiltered
  8. dissolutiondissolved in dichloromethane

Sources & evidence

ORD record
ord-ba143c861fdb4763bfbc7d36c14e43c4
Source dataset
uspto-grants-2000_05
Patent number
US06060592

Reaction notes

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