Diethylamine → HCID 86713584, compound

HRID 2274203Notes

Reaction equation

HRID 2274203 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9]2[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:18])=[N:6][CH:7]=1.[C:19]([C:21]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:29][CH3:30])[CH:22]=1)#[CH:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(NCC)C>CN(C)C=O.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.[Cu]I>[CH3:30][O:29][C:23]1[CH:22]=[C:21]([C:19]#[C:20][C:2]2[CH:3]=[N:4][C:5]([NH:8][C:9]3[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:10]=3[CH3:18])=[N:6][CH:7]=2)[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=1

Participants

8

Reactant 4

HCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 46613211-Ethynyl-3,5-dimethoxybenzeneHCID 86713583HCID 86713583, compound

Product 1

HCID 86713584HCID 86713584, compoundYield 39.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-N-(2-methyl-6-nitrophenyl)pyrimidin-2-amine (573 mg, 3.0 mmol), 1-ethynyl-3,5-dimethoxybenzene (483 mg, 3.0 mmol), triphenylphosphine (157 mg, 0.60 mmol), bis(triphenylphosphine)palladium(II) chloride (210 mg, 0.30 mmol), copper(I) iodide (57 mg, 0.30 mmol) and diethylamine (1.50 ml, 15.0 mmol) in N,N-dimethylformamide (10 mL) was degassed with nitrogen three times, and then stirred at 80° C. for 2 hrs. LCMS showed the reaction was completed. The mixture was cooled to RT, quenched with water (20 mL) and extracted with ethyl acetate (3×80 mL). The combined organic layers were separated, washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=4:1) to afford the title compound as a yellow solid (460 mg, 39%). MS (ES+) C21H18N4O4 requires: 390. Found: 391 [M+H]+.

Workup

  1. customwas degassed with nitrogen three times
  2. temperatureThe mixture was cooled to RT
  3. customquenched with water (20 mL)
  4. extractionextracted with ethyl acetate (3×80 mL)
  5. customThe combined organic layers were separated
  6. washwashed with water and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-e33ba93543584297938206510dd34613
Source dataset
uspto-grants-2015_09
Patent number
US09126951B2

Reaction notes

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