Hydrochloric Acid → N-azetidin-3-yl-2-(3-fluorophenyl)pyrimidine-5-carboxamide

HRID 729636Notes

Reaction equation

HRID 729636 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([C:14]([NH:16][CH:17]3[CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]3)=[O:15])=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl>CO.O1CCOCC1.CCOCC>[NH:19]1[CH2:20][CH:17]([NH:16][C:14]([C:11]2[CH:12]=[N:13][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:9][CH:10]=2)=[O:15])[CH2:18]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 67007696Tert-butyl 3-({[2-(3-fluorophenyl)pyrimidin-5-yl]carbonyl}amino)azetidine-1-carboxylate

Product 1

HCID 57832989N-azetidin-3-yl-2-(3-fluorophenyl)pyrimidine-5-carboxamideYield 91.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 3-({[2-(3-fluorophenyl)pyrimidin-5-yl]carbonyl}amino)azetidine-1-carboxylate (570 mg, 1.53 mmol) in methanol (1 mL) was added 4N HCl in dioxane (3 mL). The reaction mixture was stirred at room temperature overnight and then diluted with ether to give a solid, which was filtered and collected to give the desired product as the hydrochloride salt, N-azetidin-3-yl-2-(3-fluorophenyl)pyrimidine-5-carboxamide (380 mg, 72%). LC/MS (M+H)=273.2 observed, 273.12 expected.

Workup

  1. customto give a solid, which
  2. filtrationwas filtered
  3. customcollected

Sources & evidence

ORD record
ord-4bb584b8a2f541ac9e81b62d717ec1c6
Source dataset
uspto-grants-2009_09
Patent number
US07582643B2

Reaction notes

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