Sodium Carbonate → [4-(4-Methylsulfanyl-phenyl)-pyrimidin-2-yl]-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine

HRID 1434993Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)[N:3]=1.[CH3:19][S:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CC.CCOC(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>[CH3:19][S:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH:9]3[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]3)[N:3]=2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 85 °C

Procedure

The title compound was prepared according to Method C. To a degassed suspension of (4-chloro-pyrimidin-2-yl)-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine (1.07 g, 3.97 mmol) in 10 ml of 1-propanol were added bis(triphenylphosphine)palladium dichloride (112 mg, 0.16 mmol), 4-(methylthio)phenylboronic acid (1.00 g, 5.95 mmol) and 8 ml of 2N-solution of sodium carbonate. The mixture was stirred at 85° C. for 2 hours. The reaction mixture was diluted with EtOAc, filtered through Celite and washed with water. The organic layer was dried and concentrated. The solid was purified by chromatography on silicagel (EtOAc/MeOH/ammonia:66/33/1) and crystallization from n-hexane. Yield: 1.12 g (79%).

Workup

filtrationfiltered through Celite
washwashed with water
customThe organic layer was dried
concentrationconcentrated
customThe solid was purified by chromatography on silicagel (EtOAc/MeOH/ammonia:66/33/1) and crystallization from n-hexane

Sources & evidence

ORD record: ord-883c41fccd0d46e8be758bb42b611a30
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615562B2

Reaction notes

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