Potassium Carbonate → 2-[6-(4-Chloro-benzyl)-2-(2',5'-dimethyl-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-4-ylamino)-pyrimidin-4-yl]-propan-2-ol

HRID 451419Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]2)[C:5]([CH3:15])=[CH:4][N:3]=1.Cl[C:17]1[N:22]=[C:21]([C:23]([OH:26])([CH3:25])[CH3:24])[CH:20]=[C:19]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[N:18]=1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:27][C:19]2[N:18]=[C:17]([NH:14][CH:11]3[CH2:10][CH2:9][N:8]([C:6]4[C:5]([CH3:15])=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=4)[CH2:13][CH2:12]3)[N:22]=[C:21]([C:23]([OH:26])([CH3:25])[CH3:24])[CH:20]=2)=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a mixture of 2′,5′-dimethyl-3,4,5,6-tetrahydro-2H-[1,4]bipyridinyl-4-ylamine (143 mg, 0.48 mmol), 2-[2-chloro-6-(4-chloro-benzyl)-pyrimidin-4-yl]-propan-2-ol (99 mg, 0.48 mmol), finely milled potassium carbonate (100 mg, 0.72 mmol) in dioxane (2 mL) was added under an argon atmosphere palladium(II) acetate (5 mg, 0.02 mmol) and 2-(dicyclohexylphosphino)biphenyl (17 mg, 0.05 mmol) and the reaction mixture was heated at 150° C. for 30 minutes. Concentration and purification by chromatography (SiO2, n-heptane/ethyl acetate/(ethyl acetate/triethylamine=95:5)=50:50:0 to 0:80:20) afforded the title compound (67 mg, 30%) as a light brown foam.

Workup

concentrationConcentration and purification by chromatography (SiO2, n-heptane/ethyl acetate/(ethyl acetate/triethylamine=95:5)=50:50:0 to 0:80:20)

Sources & evidence

ORD record: ord-2c9241cd6edc46e994bbdb0123ab574a
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486967B2

Reaction notes

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