Triethylamine → HCID 86648167, compound

HRID 1804712Notes

Reaction equation

HRID 1804712 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[CH:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:17][C:18]1[N:23]=[C:22](Cl)[CH:21]=[CH:20][N:19]=1.C(N(CC)CC)C>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.O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]#[C:16][C:20]2[CH:21]=[CH:22][N:23]=[C:18]([Cl:17])[N:19]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 14903234'-Benzyloxyphenyl acetylene

Product 1

HCID 86648167HCID 86648167, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

Into a 250 mL round-bottomed flask was charged 1-(benzyloxy)-4-ethynylbenzene (2.0540 g, 9.86 mmol) and tetrahydrofuran (49.3 ml). 2,4-Dichloropyrimidine (1.469 g, 9.86 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.346 g, 0.493 mmol), copper(I) iodide (0.033 ml, 0.986 mmol), and triethylamine (4.12 ml, 29.6 mmol) were added. The reaction was heated to 45° C. overnight. Silica gel (approx. 15 g) was added, and the reaction concentrated. The reaction was purified by flash chromatography (10% ethyl acetate:hexanes for 10 minutes, then to 30% ethyl acetate:hexanes over 30 minutes, then to 50% ethyl acetate in hexanes over 5 minutes, then to 100% ethyl acetate over 5 minutes.) to provide the title compound. MS (ESI) m/e 321 (M+H)+.

Workup

  1. additionSilica gel (approx. 15 g) was added
  2. concentrationthe reaction concentrated
  3. customThe reaction was purified by flash chromatography (10% ethyl acetate
  4. waitto 30% ethyl acetate:hexanes over 30 minutes
  5. waitto 50% ethyl acetate in hexanes over 5 minutes
  6. waitto 100% ethyl acetate over 5 minutes

Sources & evidence

ORD record
ord-047215fe79404d8489ed5549beca286f
Source dataset
uspto-grants-2013_01
Patent number
US08354422B2

Reaction notes

Loading…