4-(6-Methoxy-pyrimidin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester → 4-Methoxy-6-piperidin-4-yl-pyrimidine

HRID 400424Notes

Reaction equation

HRID 400424 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:21][O:20][C:18]1[CH:19]=[C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[N:15]=[CH:16][N:17]=1

Participants

5

Reactant 1

HCID 866860314-(6-Methoxy-pyrimidin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 826566604-Methoxy-6-piperidin-4-yl-pyrimidineYield 31.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

1.16 g 4-(6-Methoxy-pyrimidin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester were stirred in 2 mL 4 mol/L HCl solution in dioxane for 40 min. The mixture was diluted with dioxane and basified with sodiumcarbonate. The suspension was filtered and the filtrate was concentrated to give 0.24 g of the desired product.

Workup

  1. filtrationThe suspension was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c1ed6236f76444be968135cc09aec311
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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