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

HRID 563859Notes

Reaction equation

HRID 563859 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-4c3209ecbce944edae2ee7b3d568660a
Source dataset
uspto-grants-2011_11
Patent number
US08067589B2

Reaction notes

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