Methylamine → Tert-butyl 1'-[6-(methylamino)pyrimidin-4-yl]-4,4'-bipiperidine-1-carboxylate

HRID 2093459Notes

Reaction equation

HRID 2093459 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)[CH:3]=1.[CH3:27][NH2:28]>CO>[CH3:27][NH:28][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)[CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59178818HCID 59178818, compound

Product 1

HCID 59178837Tert-butyl 1'-[6-(methylamino)pyrimidin-4-yl]-4,4'-bipiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

The tert-butyl 1′-(6-chloropyrimidin-4-yl)-4,4′-bipiperidine-1-carboxylate (19 mg, 0.05 mmol) was added to methyl amine in MeOH (1N, 2 mL) in a sealed bottle and heated to 50° C. for 2 days. The reaction crude were cooled down to r.t. and concentrated on rotavapor. The crude mixture was purified by preparative TLC with 10% methanol: dichloromethane to yield title compound.

Workup

  1. customThe reaction crude
  2. temperaturewere cooled down to r.t.
  3. concentrationconcentrated on rotavapor
  4. customThe crude mixture was purified by preparative TLC with 10% methanol

Sources & evidence

ORD record
ord-05527008a37240ab9b135666975dbe17
Source dataset
uspto-grants-2013_05
Patent number
US08445499B2

Reaction notes

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