1-Phenethylamine, (-)- → HCID 21023644, compound
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[N:13]=[C:12]([N:14]3[CH2:18][CH2:17][CH2:16][CH:15]3[CH2:19][O:20][CH3:21])[N:11]([CH3:22])[C:10](=[O:23])[C:9]=2[C:24]2[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=2)[CH:5]=[CH:4][N:3]=1.[CH3:31][C@H:32]([NH2:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[CH3:21][O:20][CH2:19][CH:15]1[CH2:16][CH2:17][CH2:18][N:14]1[C:12]1[N:11]([CH3:22])[C:10](=[O:23])[C:9]([C:24]2[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=2)=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:39][CH:32]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH3:31])[CH:7]=2)[N:13]=1Participants
7
Conditions
- Temperature
- 100 °C
Procedure
To a 100 mL RBF, was added 6-(2-chloro-pyridin-4-yl)-2-(2-methoxymethyl-pyrrolidin-1-yl)-3-methyl-5-m-tolyl-3H-pyrimidin-4-one (0.3 g, 0.71 mmol), 50 mL toluene, and (S)-α-methyl benzylamine (0.181 mL, 1.42 mmol). The mixture was degassed by nitrogen bubbled through for 1 h. After added Pd(OAc)2 (24 mg, 0.106 mmol), BINAP (65 mg, 0.106 mmol) and NaOtBu (0.191 g, 2.0 mmol), the mixture was warmed up to 100° C. and stirred for 3 h under nitrogen. The mixture was cooled down to rt, and vacuumed down all volatile composites. After purified by flash chromatography, the title compound was obtained in 0.18 g as pale yellow solid. MS (ES+): 510 (M+H)+.
Workup
- customThe mixture was degassed by nitrogen
- custombubbled through for 1 h
- temperatureThe mixture was cooled down to rt
- customAfter purified by flash chromatography
Sources & evidence
- ORD record
- ord-13c64723dd274cc480c7f4b252274686
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07026326B2
Reaction notes
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