Water → (1S)-(2,4-Dichloro-6-methyl-pyrimidin-5-ylmethyl)methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amine

HRID 1455746Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH2:9]Cl)=[C:4]([CH3:11])[N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:18][NH:19][C@@H:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22][CH2:21]1.O>CCO.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH2:9][N:19]([CH3:18])[C@@H:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:23][CH2:22][CH2:21]2)=[C:4]([CH3:11])[N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a flask containing 2,4-dichloro-5-chloromethyl-6-methyl-pyrimidine (107 mg, 0.51 mmol) in absolute EtOH (10 mL) is added K2CO3 (70 mg, 1.0 eq., 0.51 mmol) and the reaction is cooled to 0° C. with an ice bath. (1S)-Methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)amine (82 mg, 1.0 equiv, 0.51mmol) in 1.0 mL of EtOH is added via syringe in one portion and allowed to warm to ambient temperature over 3 h. Water (50 mL) and EtOAc (50 mL) is added and the EtOAc layer is washed with water (100 mL) and brine (50 mL) and dried over Na2SO4. Concentration and vacuum drying affords the title compound as a yellow gum. [mass expected (336.26); mass found (336.30)]

Workup

temperatureto warm to ambient temperature over 3 h
washthe EtOAc layer is washed with water (100 mL) and brine (50 mL)
dry with materialdried over Na2SO4
concentrationConcentration and vacuum
customdrying

Sources & evidence

ORD record: ord-b190051fb5374cbc83c961144f359681
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482350B2

Reaction notes

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