N-Methylbenzylamine → HCID 60024763, compound

HRID 586427Notes

Reaction equation

CC(C)([O-])C.[Na+].Br[C:8]1[CH:9]=[C:10]([NH:15][C:16]2[CH:21]=[C:20]([N:22]([CH3:24])[CH3:23])[N:19]=[C:18]([N:25]3[CH2:30][C@H:29]([CH3:31])[O:28][C@H:27]([CH3:32])[CH2:26]3)[N:17]=2)[CH:11]=[CH:12][C:13]=1[CH3:14].[CH3:33][NH:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O1CCCC1.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>[CH2:35]([N:34]([CH3:33])[C:8]1[CH:9]=[C:10]([NH:15][C:16]2[CH:21]=[C:20]([N:22]([CH3:24])[CH3:23])[N:19]=[C:18]([N:25]3[CH2:30][C@H:29]([CH3:31])[O:28][C@H:27]([CH3:32])[CH2:26]3)[N:17]=2)[CH:11]=[CH:12][C:13]=1[CH3:14])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Sodium tert-butoxide (60 mg, 0.63 mmol) was added to a solution of N4-(3-bromo-4-methylphenyl)-2-(cis-2,6-dimethylmorpholinyl)-N6,N6-dimethyl-4,6-pyrimidinediamine (50 mg, 0.12 mmol) and N-methyl(phenyl)methanamine (50 mg, 0.40 mmol) in tetrahydrofuran (2 mL). Tris(dibenzylidineacetone)dipalladium (1 mg, 0.001 mmol) and 2,2′-bis(diphenylphosphino)-1,1′-binapthyl (2 mg, 0.003 mmol) were added to this mixture and the resulting mixture was heated at 110° C. for 16 hours. The mixture was then cooled to room temperature, concentrated in vacuo, and purified by preparative thin-layer chromatography [eluent: hexane/EtOAc (3:1)], giving the desired product (20 mg, 36%).

Workup

temperatureThe mixture was then cooled to room temperature
concentrationconcentrated in vacuo
custompurified by preparative thin-layer chromatography [eluent: hexane/EtOAc (3:1)]

Sources & evidence

ORD record: ord-4f061355f82b4feb8885486e1dca6919
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06936607B2

Reaction notes

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