Hydrochloric Acid → HCID 66589876, compound

HRID 1911450Notes

Reaction equation

HRID 1911450 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-e1d2800a9b6041649c5ef45a548f84cf
Source dataset
uspto-grants-2013_12
Patent number
US08604022B2

Reaction notes

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