Acetonitrile → HCID 11723338, compound

HRID 2056248Notes

Reaction equation

HRID 2056248 reaction equation
[CH2:1]([C:3]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:9]=[C:8]2[C:4]=1[NH:5][CH:6]=[N:7]2)[CH3:2].[C:16]([C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1)#[N:17].C(N(CC)CC)C.C(#N)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(OCC)(=O)C>[C:16]([C:18]1[CH:23]=[C:22]([N:7]2[CH:6]=[N:5][C:4]3[C:8]2=[N:9][C:10]([C:12]([F:14])([F:15])[F:13])=[N:11][C:3]=3[CH2:1][CH3:2])[CH:21]=[CH:20][CH:19]=1)#[N:17]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 27343253-Cyanophenylboronic acidHCID 45095225HCID 45095225, compound

Product 1

HCID 11723338HCID 11723338, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
52.5 °C

Procedure

A mixture of 6-ethyl-2-trifluoromethylpurine (86 mg, 0.40 mmol), 3-cyanophenylboronic acid (103 mg, 0.70 mmol), copper (II) acetate (72 mg, 0.4 mmol), triethylamine (202 mg, 2.0 mmoL), anhydrous acetonitrile (5 ml) and molecular sieves (˜10 pellets) was stirred at 50-55° C. for 18 hours. Ethyl acetate (20 ml) was added and the solid was filtered off. The filtrate was washed with 20 ml of 5% aqueous sodium bicarbonate, concentrated under vacuum, and purified by chromatography over SiO2 (ethyl acetate/hexane 1:3) to give 24 mg of 9-(3-cyanophenyl)-6-ethyl-2-trifluoromethylpurine (yield 19%). 1H NMR (300 MHz, CDCl3) δ 8.50 (s, 1H), 8.11 (m, 2H), 7.82(m, 2H), 3.35 (q, J=7.5 Hz, 2H), 1.50 (t, J=7.5 Hz, 3H). [ESMS m/z (318.4 (M+H)+)]

Workup

  1. filtrationthe solid was filtered off
  2. washThe filtrate was washed with 20 ml of 5% aqueous sodium bicarbonate
  3. concentrationconcentrated under vacuum
  4. custompurified by chromatography over SiO2 (ethyl acetate/hexane 1:3)

Sources & evidence

ORD record
ord-3fe03f1bac6a4f8393590cdbf21da877
Source dataset
uspto-grants-2008_02
Patent number
US07335654B2

Reaction notes

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