Oxygen → HCID 86611667, compound

HRID 2261521Notes

Reaction equation

HRID 2261521 reaction equation
C(N(CC)CC)C.O=O.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C@:17]2([O:26][C@H:25]([CH2:27][OH:28])[C@@H:23]([OH:24])[C@H:21]([OH:22])[C@H:19]2[OH:20])[OH:18])=[CH:13][C:12]=1[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]#[CH:37])=[CH:32][CH:31]=1.Br[C:39]1[CH:40]=[N:41][CH:42]=[N:43][CH:44]=1>CN(C)C=O.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C@:17]2([O:26][C@H:25]([CH2:27][OH:28])[C@@H:23]([OH:24])[C@H:21]([OH:22])[C@H:19]2[OH:20])[OH:18])=[CH:13][C:12]=1[CH2:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]#[C:37][C:39]2[CH:40]=[N:41][CH:42]=[N:43][CH:44]=2)=[CH:34][CH:35]=1

Participants

8

Reactant 4

HCID 977OxygenHCID 8471TriethylamineHCID 783445-BromopyrimidineHCID 866006811-Chloro-2-(4-ethynyl-benzyl)-4-(beta-D-glucopyranos-1-yl)-benzene

Product 1

HCID 86611667HCID 86611667, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

37 mg copper iodide, 67 mg bis-(triphenylphosphine)-palladium dichloride and 0.46 mL triethylamine are added to an oxygen-free solution of 0.35 g 1-chloro-4-(β-D-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene and 0.2 g 5-bromo-pyrimidine in 1 mL dimethylformamide. The solution is stirred under argon atmosphere at 60° C. for 16 h. The reaction mixture is filtered through Celite and evaporated down. The residue is chromatographed on silica gel (dichloromethane/methanol 1:0→9:1).

Workup

  1. filtrationThe reaction mixture is filtered through Celite
  2. customevaporated down
  3. customThe residue is chromatographed on silica gel (dichloromethane/methanol 1:0→9:1)

Sources & evidence

ORD record
ord-39e6d2a6e6844dd49d619e2d3d55e7fd
Source dataset
uspto-grants-2010_12
Patent number
US07847074B2

Reaction notes

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