1,4-Dioxane → HCID 86726465, compound

HRID 529693Notes

Reaction equation

HRID 529693 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([O:20][CH:21]([CH3:23])[CH3:22])[C:5]2[C:10](I)=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]=2[N:7]=1.CC1([CH2+])C(C)(C)OB([C:32]2[CH:37]=[CH:36][C:35]([C:38]3[N:39]([CH2:43][O:44][CH2:45][CH2:46][Si:47]([CH3:50])([CH3:49])[CH3:48])[CH:40]=[CH:41][N:42]=3)=[CH:34][CH:33]=2)O1.O.O.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>O>[Cl:1][C:2]1[N:3]=[C:4]([O:20][CH:21]([CH3:23])[CH3:22])[C:5]2[C:10]([C:32]3[CH:33]=[CH:34][C:35]([C:38]4[N:39]([CH2:43][O:44][CH2:45][CH2:46][Si:47]([CH3:50])([CH3:49])[CH3:48])[CH:40]=[CH:41][N:42]=4)=[CH:36][CH:37]=3)=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 18407952Tripotassium phosphate trihydrateHCID 86726464HCID 86726464, compoundHCID 86726466HCID 86726466, compound

Product 1

HCID 86726465HCID 86726465, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a degassed mixture of 2-chloro-5-iodo-4-isopropoxy-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (1 equiv), (4,5,5-trimethyl-2-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)-1,3,2-dioxaborolan-4-yl)methylium (1.2 equiv) and tripotassium phosphate trihydrate (3 equiv) in a 9:1 mixture of 1,4-dioxane and water (0.09 M) was added palladium 1,1-bis(diphenylphosphion)-ferrocene dichloride (0.2 equiv). The reaction mixture was stirred at 100° C. for 2 h. After the reaction was complete, the reaction mixture was cooled to room temperature and concentrated. The residue was purified by silica gel chromatography (0-20% ethyl acetate in petroleum ether) to afford the title compound (82% yield) as a red solid. MS (ESI) m/z 614.2 [M+1]+.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography (0-20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-940746a95d9e4ce2a536a10766b3eb88
Source dataset
uspto-grants-2016_05
Patent number
US09346812B2

Reaction notes

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