Sodium hydride → HCID 23568302, compound

HRID 1822624Notes

Reaction equation

HRID 1822624 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[C:24](=[O:25])[C:23]([CH3:26])=[CH:22][N:12]([C@@H:13]2[O:21][C@H:18]([CH2:19][OH:20])[C@@H:16]([OH:17])[C@H:14]2[OH:15])[C:11]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:31][CH2:32][CH2:33][CH2:34][Cl:35]>>[CH2:1]([O:8][CH2:9][N:10]1[C:24](=[O:25])[C:23]([CH3:26])=[CH:22][N:12]([C@@H:13]2[O:21][C@H:18]([CH2:19][OH:20])[C@@H:16]([OH:17])[C@H:14]2[O:15][CH2:31][CH2:32][CH2:33][CH2:34][Cl:35])[C:11]1=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutaneHCID 110362233-Benzyloxymethyl-5-methyluridine

Product 1

HCID 23568302HCID 23568302, compoundYield 41%

Procedure

A solution of 3-benzyloxymethyl-5-methyluridine (25.9 g, 68 mmol) was treated with NaH (60% oil, 7.9 g, 200 mmol) for 1 hr at room temp. 1-Bromo-4-chlorobutane (19.7 g, 115 mmol) was added slowly and the reaction stirred at room temp. for 16 hrs. The reaction was then quenched (MeOH), concentrated in vacuo and the residue chromatographed on silica gel CHCl3/MeOH 95/5 to give the title compound in 41% yield. 1H NMR (DMSO-d6) δ 5.87 (d, 1H, C1′H).

Workup

  1. customThe reaction was then quenched (MeOH)
  2. concentrationconcentrated in vacuo
  3. customthe residue chromatographed on silica gel CHCl3/MeOH 95/5

Sources & evidence

ORD record
ord-2146565f51b14380b6ac1ae484262eaa
Source dataset
uspto-grants-2006_05
Patent number
US07037646B1

Reaction notes

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