2,4-Dichloro-6-methylpyrimidine → 1-(2-Chloro-6-methylpyrimidin-4-yl)-1'-(5-methylpyrazin-2-yl)-4,4'-bipiperidine

HRID 2093480Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[Cl:20][C:21]1[N:26]=[C:25](Cl)[CH:24]=[C:23]([CH3:28])[N:22]=1.N12CCCN=C1CCCCC2>CN1C(=O)CCC1.C(OCC)(=O)C>[Cl:20][C:21]1[N:26]=[C:25]([N:17]2[CH2:18][CH2:19][CH:14]([CH:11]3[CH2:12][CH2:13][N:8]([C:5]4[CH:4]=[N:3][C:2]([CH3:1])=[CH:7][N:6]=4)[CH2:9][CH2:10]3)[CH2:15][CH2:16]2)[CH:24]=[C:23]([CH3:28])[N:22]=1

Participants

Conditions

Temperature: -20 °C

Procedure

The 1-(5-methylpyrazin-2-yl)-4,4′-bipiperidine (720 mg, 2.8 mmol) and 2,4-dichloro-6-methyl-pyrimidine (502 mg, 3.1 mmol) were dissolved in NMP (30 mL), and the solution cooled to −20° C. The 1,8-diazabicyclo[5.4.0]-undec-7-ene (4.2 mL, 28 mmol) was added drop-wise and the solution stirred for 10 minutes. The mixture was diluted with ethyl acetate (50 mL), washed with brine (30 mL×2), dried over magnesium sulfate, filtered and concentrated in vac. The residue was purified by chromatography on silica gel with 30% acetone: hexanes to yield the title compound.

Workup

washwashed with brine (30 mL×2)
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vac
customThe residue was purified by chromatography on silica gel with 30% acetone

Sources & evidence

ORD record: ord-5d0311e5d1df4c9e9efd99c2e280c768
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445499B2

Reaction notes

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