3-Butyn-2-amine, 2-methyl- → {4-[4-(3-Amino-3-methyl-but-1-ynyl)-phenyl]-pyrimidin-2-yl}-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine

HRID 1434998Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH:15]3[CH2:20][C:19]([CH3:22])([CH3:21])[NH:18][C:17]([CH3:24])([CH3:23])[CH2:16]3)[N:9]=2)=[CH:4][CH:3]=1.[CH3:25][C:26]([NH2:30])([CH3:29])[C:27]#[CH:28]>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>[NH2:30][C:26]([CH3:29])([CH3:25])[C:27]#[C:28][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH:15]3[CH2:20][C:19]([CH3:22])([CH3:21])[NH:18][C:17]([CH3:24])([CH3:23])[CH2:16]3)[N:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of [4-(4-bromo-phenyl)-pyrimidin-2-yl]-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine (62 mg, 0.16 mmol) (Example 180) in 10 ml triethylamine were added bis(triphenylphosphine)palladium dichloride (22 mg, 0.03 mmol), 1,1-dimethyl-prop-2-ynylamine (166 μl, 1.43 mmol) and CuI (9.5 mg, 0.05 mmol). The mixture was stirred at 95° C. for 16 hours. The reaction mixture was concentrated, the residue taken up in EtOAc and the organic phase was washed with water. The organic layer was dried and concentrated. Purification using preparative HPLC gave the title compound. Yield: 26 mg (42%).

Workup

concentrationThe reaction mixture was concentrated
washthe organic phase was washed with water
customThe organic layer was dried
concentrationconcentrated
customPurification

Sources & evidence

ORD record: ord-08bd63e1baaa41749d152f1d25557755
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615562B2

Reaction notes

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