Hydrochloric Acid → HCID 66589876, compound

HRID 16878Notes

Reaction equation

HRID 16878 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[N:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][N:16]=2)[CH2:11][CH2:10]1)=O)(C)(C)C>CO>[NH:9]1[CH2:14][CH2:13][CH:12]([C:15]2[N:16]=[CH:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:20]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66589682HCID 66589682, compound

Product 1

HCID 66589876HCID 66589876, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrogen chloride (4M in 1,4-dioxane, 3.04 ml, 12.15 mmol) was added to a stirred suspension of methyl 2-(1-(tert-butoxycarbonyl)piperidin-4-yl)pyrimidine-5-carboxylate (976 mg, 3.04 mmol) in methanol (15.20 ml) at 25° C. The resulting solution was stirred at ambient temperature for 18 hours. The reaction mixture was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and evaporated to dryness to afford methyl 2-(piperidin-4-yl)pyrimidine-5-carboxylate (600 mg, 89%) as a yellow solid. This was used directly with no further purification.

Workup

  1. customThe reaction mixture was purified by ion exchange chromatography
  2. washThe desired product was eluted from the column
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-70783275b870460a8735a9f0bc5d414e
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Reaction notes

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