Sodium Carbonate → 5-Bromo-N4-(1-methylpiperidin-4-yl)pyridine-2,4-diamine

HRID 384681

Reaction equation

HRID 384681 reaction equation
[Br:1][C:2]1[C:3]([NH:15][CH:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)=[CH:4][C:5]([NH:8]C(=O)C(C)(C)C)=[N:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl>[Br:1][C:2]1[C:3]([NH:15][CH:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 59613507N-(5-Bromo-4-(1-methylpiperidin-4-ylamino)pyridin-2-yl)pivalamide

Product 1

HCID 596135485-Bromo-N4-(1-methylpiperidin-4-yl)pyridine-2,4-diamineYield 71.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-(5-bromo-4-(1-methylpiperidin-4-ylamino)pyridin-2-yl)pivalamide (0.526, 1.42 mmol) in 6M HCl (6 mL) was heated under microwave irradiation at 105° C. for 50 min. The solution was basified with Na2CO3 and extracted with ethyl acetate (3×20 mL). The crude mixture was purified by flash chromatography on silica, eluting with methanol and dichloromethane (1/9), to give the title compound as a colourless solid (0.288 g, 70%).

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. customThe crude mixture was purified by flash chromatography on silica
  3. washeluting with methanol and dichloromethane (1/9)

Sources & evidence

ORD record
ord-ce1e854115f341c2aa1ea09795094869
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Linked notes

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