Pyridine → HCID 68650701, compound

HRID 646750Notes

Reaction equation

HRID 646750 reaction equation
[NH2:1][C:2]1[CH:3]([C:17]([O:19][CH3:20])=[O:18])[N:4]([CH3:16])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14]O)[CH:9]=2)=[CH:6][N:7]=1.N1C=CC=CC=1.S(Cl)([Cl:29])=O>C1COCC1>[NH2:1][C:2]1[CH:3]([C:17]([O:19][CH3:20])=[O:18])[N:4]([CH3:16])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][Cl:29])[CH:9]=2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 68650200HCID 68650200, compound

Product 1

HCID 68650701HCID 68650701, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 3-amino-6-(3-hydroxymethylphenyl)-N-methylpyrazine-2-carboxylate (75 mg, 0.3 mmol) was taken into THF (2 mL) followed by addition of pyridine (120 uL, 1.5 mmol) and the solution was cooled to 0° C. Thionyl chloride (42 uL, 0.6 mmol) was added to the mixture by syringe followed by warming to room temperature. The mixture was then stirred for two hours and partitioned with ethyl acetate and 1 M aqueous hydrochloric acid. The organic layer was washed with water (1x) then brine and dried over anhydrous sodium sulfate. The mixture was filtered and concentrated followed by silica gel flash chromatography using ethyl acetate:hexanes (1:1) as eluent. The pure fractions were combined and concentrated then dried in vacuo to give methyl 3-amino-6-(3-chloromethylphenyl)-N-methylpyrazine-2-carboxylate (30 mg, 37% yield) as a yellow solid: MS (EI) for C13H13N3O2Cl: 278, 280 (MH+).

Workup

  1. temperatureby warming to room temperature
  2. custompartitioned with ethyl acetate and 1 M aqueous hydrochloric acid
  3. washThe organic layer was washed with water (1x)
  4. dry with materialbrine and dried over anhydrous sodium sulfate
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated
  7. concentrationconcentrated
  8. customthen dried in vacuo

Sources & evidence

ORD record
ord-7c56825397b44d5d986f3ab4f774200c
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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