Aminopyrazine → HCID 59436391, compound

HRID 1961420Notes

Reaction equation

HRID 1961420 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH2:7].C([Mg]Cl)(C)C.[N:13]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16][CH2:15][C@H:14]1[C:17](OC)=[O:18]>C1COCC1>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:7][C:17]([C@@H:14]1[CH2:15][CH2:16][N:13]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:18]

Participants

5

Reactant 3

HCID 78747AminopyrazineHCID 148217361-tert-Butyl 2-methyl (2S)-azetidine-1,2-dicarboxylateHCID 178418918HCID 178418918, compound

Product 1

HCID 59436391HCID 59436391, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of pyrazin-2-amine (1.626 g, 17.10 mmol) in THF (40 mL) was added isopropylmagnesium chloride (8.44 mL, 16.88 mmol) at 0° C. under N2. The resulting slurry was stirred at RT for 30 min. A solution of (S)-1-tert-butyl 2-methyl azetidine-1,2-dicarboxylate (0.92 g, 4.27 mmol) in THF (5 ml) was added to the reaction slurry. The reaction mixture was stirred at RT for 4 h. and concentrated. The residue was dissolved in EtOAc and washed with 1N HCl, water, and brine. The organic layer was dried over Na2SO4 and filtered. The crude product (1.05 g, 88%) was used in the next step without purification. 1H NMR (400 MHz, MeOD) δ ppm 1.38 (s, 9H) 2.31 (br s, 1H) 2.53 (ddd, J=8.81, 6.17, 2.39 Hz, 1H) 3.89-4.00 (m, 2H) 4.81-4.86 (m, 1H) 8.30-8.37 (m, 2H) 9.41 (s, 1H); LC/MS [M+H]+: 279; Ret time (Method F): 2.27 min.

Workup

  1. stirringThe reaction mixture was stirred at RT for 4 h.
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with 1N HCl, water, and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customThe crude product (1.05 g, 88%) was used in the next step without purification
  8. custom2.27 min.

Sources & evidence

ORD record
ord-c213745a0ede4e96b3082862d97e41a9
Source dataset
uspto-grants-2013_04
Patent number
US08415340B2

Reaction notes

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