Purine → HCID 21940652, compound

HRID 1883419Notes

Reaction equation

HRID 1883419 reaction equation
[N:1]1[CH:9]=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.I[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[Cs+].[Cs+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.CCCCCC.C(OCC)(=O)C.CN(C)C=O>[C:11]1([N:1]2[CH:9]=[C:8]3[C:4](=[N:5][CH:6]=[N:7]3)[N:3]=[CH:2]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 1044PurineHCID 10796Cesium carbonateHCID 11575IodobenzeneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 21940652HCID 21940652, compoundYield 69.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Using the general procedure, purine (0.120 g, 1.00 mmol) was coupled with iodobenzene (225 μL, 2.00 mmol) using CuI (9.5 mg, 0.050 mmol, 5.0 mol %), Cs2CO3 (2.1 mmol), trans-N,N′-dimethyl-1,2-cyclohexanediamine (32 μL, 0.20 mmol, 20 mol %) and dimethylformamide (1.0 mL) to give the crude product. Column chromatography (2×15 cm, hexane:ethyl acetate 1:2) provided 0.136 g (69% yield) of the product as a white solid. 1H NMR (400 MHz, CDCl3): δ8.00 (d, J=0.9 Hz, 1H), 7.52 (m, 3H), 7.42 (m, 5H), 6.73 (dd, J=0.6 Hz and J=3.3 Hz, 1H), 7.60 (m, 2H), 7.48 (m, 1H).

Workup

  1. customto give the crude product

Sources & evidence

ORD record
ord-19939af0f44a410cb80e7bf31b797204
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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