Triethylamine → HCID 90039660, compound

HRID 1497350Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH:12]3[CH2:13][CH2:14][CH2:15][CH:11]3[N:10]([CH2:16][CH3:17])[C:9]2=[O:18])=[N:6][CH:7]=1.[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)#[CH:20].C(N(CC)CC)C>CN(C=O)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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:16]([N:10]1[CH:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[N:8]([C:5]2[N:4]=[CH:3][C:2]([C:20]#[C:19][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:7][N:6]=2)[C:9]1=[O:18])[CH3:17]

Participants

Conditions

Temperature: 75 °C

Procedure

In a microwave tube were dissolved 80 mg (0.26 mmol) of (rac)-1-(5-bromopyrimidin-2-yl)-3-ethylhexahydrocyclopenta[d]imidazol-2(1H)-one (Example 1, step 4) in 3 ml DMF. Argon was bubbled through the solution. Ethynylbenzene (57 μl, 53 mg, 0.52 mmol, 2 equiv.), Bis(triphenylphosphine)palladium(II) chloride (9 mg, 0.013 mmol, 0.05 equiv.), copper (I) iodide (1.5 mg, 7.7 μmol, 0.03 equiv.), triphenylphosphine (2.0 mg, 7.7 μmol, 0.03 equiv.) and 107 μl of triethylamine (78 mg, 0.77 mmol, 3 equiv.) were added. The dark brown solution was stirred at 75° C. overnight, adsorbed on silica and purified by flash chromatography (silica gel, 20 g, 0% to 80% EtOAc in heptane gradient) to yield 72.7 mg (85%) of the title compound as a brown solid, MS: m/e=333.3 (M+H+).

Workup

customArgon was bubbled through the solution
custompurified by flash chromatography (silica gel, 20 g, 0% to 80% EtOAc in heptane gradient)

Sources & evidence

ORD record: ord-7284133fec5346b09c5ad665f45cd313
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199971B2

Reaction notes

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