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

HRID 1947659Notes

Reaction equation

HRID 1947659 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-f5ec409f2b594d95abfe2575306eb2b1
Source dataset
uspto-grants-2013_03
Patent number
US08399485B2

Reaction notes

Loading…