Water → HCID 69081211, compound

HRID 2056245Notes

Reaction equation

HRID 2056245 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH3:3].Cl[C:7]1[N:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[N:13]=[C:12]2[C:8]=1[NH:9][CH:10]=[N:11]2.C1COCC1.O>C(OCC)(=O)C.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([C:7]1[N:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[N:13]=[C:12]2[C:8]=1[NH:9][CH:10]=[N:11]2)[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 60539116-chloro-2-(trifluoromethyl)-7H-purineHCID 178455851HCID 178455851, compound

Product 1

HCID 69081211HCID 69081211, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 178418745HCID 178418745, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

1-Propyl magnesium bromide (3.0 mmol) was added to a mixture of 6-chloro-2-trifluoromethylpurine 222 mg (1.0 mmol), [1,3-bis(diphenylphosphino)-propane]dichloronickel(II) (0.04 mmol) and THF 15 ml at 20° C. under nitrogen. The reaction mixture was allowed to stirred at 50° C. for 12 hours, then cooled to 20 ° C., and 0.2 ml of water was added to quench the reaction. The mixture was diluted with 20 ml ethyl acetate and filtered over celite. Evaporation under vacuo and chromatography (MeOH:EtOAc:hexane=2:50:50) gave the title compound with 30% yield. 1H NMR (300 MHz, CDCl3) δ 8.10 (s, 1H), 7.27 (t, J=8.37 Hz, 1H), 3.29 (t, J=7.5 Hz, 2H), 1.95 (m,2H), 1.02 (t, 7.5 Hz, 2H).

Workup

  1. temperaturecooled to 20 ° C.
  2. customto quench
  3. customthe reaction
  4. filtrationfiltered over celite
  5. customEvaporation under vacuo and chromatography (MeOH:EtOAc:hexane=2:50:50)

Sources & evidence

ORD record
ord-df4416aaae82483e8950c83cbcb1627c
Source dataset
uspto-grants-2008_02
Patent number
US07335654B2

Reaction notes

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