Ammonium Chloride → HCID 58075693, compound

HRID 2370217Notes

Reaction equation

HRID 2370217 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10]C)=O)[CH:5]=[C:4]([NH:12][CH3:13])[N:3]=1.Cl.[CH3:15][NH:16][O:17][CH3:18].C([Mg]Cl)(C)C.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([N:16]([O:17][CH3:18])[CH3:15])=[O:10])[CH:5]=[C:4]([NH:12][CH3:13])[N:3]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 58075361HCID 58075361, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 58075693HCID 58075693, compoundYield 35.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-10 °C

Procedure

To a suspension of methyl 2-chloro-6-(methylamino)pyrimidine-4-carboxylate (1.95 g) and N,O-dimethylhydroxylamine hydrochloride (1.887 g, 19.34 mmol) in THF at −20° C. was added isopropylmagnesium chloride (23.60 mL, 47.2 mmol) dropwise through a dropping funnel over a period of 30 min, and the reaction mixture was stirred at −10° C. for 40 min. The reaction was worked up with sat. NH4Cl and EtOAc, and the crude product was purified by Biotage eluting with 40-90% EtOAc/Hexanes to give the title compound as a colorless oil (786 mg). LC-MS (M+H)+=231.01.

Workup

  1. customthe crude product was purified by Biotage
  2. washeluting with 40-90% EtOAc/Hexanes

Sources & evidence

ORD record
ord-d3a9f1c7e01a4d7bb942a6a7fa2f97db
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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