Binap, (A+-)- → HCID 20825590, compound

HRID 586413Notes

Reaction equation

CC(C)([O-])C.[Na+].[CH:7]([NH:10][C:11]1[C:12]([NH2:18])=[CH:13][CH:14]=[C:15]([CH3:17])[CH:16]=1)([CH3:9])[CH3:8].Cl[C:20]1[N:25]=[C:24]([N:26]2[CH2:31][CH2:30][N:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[CH2:28][CH2:27]2)[N:23]=[C:22]([N:38]([CH3:40])[CH3:39])[CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1>[CH:7]([NH:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=1[NH:18][C:20]1[CH:21]=[C:22]([N:38]([CH3:40])[CH3:39])[N:23]=[C:24]([N:26]2[CH2:31][CH2:30][N:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[CH2:28][CH2:27]2)[N:25]=1)([CH3:9])[CH3:8]

Participants

Conditions

Temperature: 110 °C

Procedure

Sodium tert-butoxide (100 mg, 1.04 mmol) was added to a solution of N2-isopropyl-4-methyl-1,2-benzenediamine (100 mg 0.60 mmol) and N-{6-chloro-2-[4-(2-pyridinyl)-1-piperazinyl]-4-pyrimidinyl}-N,N-dimethylamine (100 mg, 0.30 mmol) in 1,4-dioxane (10 mL). Tris(dibenzylidineacetone)dipalladium (8 mg, 0.008 mmol) and 2,2′-Bis(diphenylphosphino)-1,1′binapthyl (10 mg, 0.016 mmol) were added to this mixture and heated at 110° C. for 10 hours. The resulting mixture was cooled to room temperature, concentrated in vacuo, and purified by preparative thin-layer chromatography [eluent: hexane/EtOAc (1:1)], giving the desired product (30 mg, 23%).

Workup

temperatureThe resulting mixture was cooled to room temperature
concentrationconcentrated in vacuo
custompurified by preparative thin-layer chromatography [eluent: hexane/EtOAc (1:1)]

Sources & evidence

ORD record: ord-e99148fb90fa456b9b03bd9154668fb6
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06936607B2

Reaction notes

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