4-(6-Acetylamino-2-chloro-pyrimidin-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester → N-[2-Chloro-6-(piperidin-4-ylamino)-pyrimidin-4-yl]-acetamide dihydrochloride

HRID 2426558Notes

Reaction equation

HRID 2426558 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[C:19]([NH:21][C:22](=[O:24])[CH3:23])[N:18]=[C:17]([Cl:25])[N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)C.Cl.O1CCOCC1>[ClH:25].[ClH:25].[Cl:25][C:17]1[N:18]=[C:19]([NH:21][C:22](=[O:24])[CH3:23])[CH:20]=[C:15]([NH:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[N:16]=1

Participants

5

Reactant 1

HCID 866185454-(6-Acetylamino-2-chloro-pyrimidin-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86618546N-[2-Chloro-6-(piperidin-4-ylamino)-pyrimidin-4-yl]-acetamide dihydrochloride

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-(6-acetylamino-2-chloro-pyrimidin-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (0.1 g, 0.27 mmol) in ethanol (2 mL) and 4 M HCl in dioxane (2 mL) was stirred at rt for 2 h. The solvent was removed under reduced pressure and the crude product used in the consecutive step without further purification assuming quantitative deprotection and formation of the dihydrochloride salt. MS (ISP): 270.0 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product used in the consecutive step without further purification

Sources & evidence

ORD record
ord-55085bc4b5844ce4b0abf59cff978985
Source dataset
uspto-grants-2011_06
Patent number
US07968568B2

Reaction notes

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