Sodium hydride → HCID 16125027, compound

HRID 1373745Notes

Reaction equation

HRID 1373745 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[CH2:4][CH:5]=[CH2:6].[NH2:8][C:9]1[CH:14]=[N:13][CH:12]=[C:11](Cl)[N:10]=1>O1CCOCC1.C(OCC)(=O)C>[CH2:3]([O:7][C:11]1[N:10]=[C:9]([NH2:8])[CH:14]=[N:13][CH:12]=1)[CH2:4][CH:5]=[CH2:6]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 693893-Buten-1-olHCID 1184582-Amino-6-Chloropyrazine

Product 1

HCID 16125027HCID 16125027, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of NaH (60%, 618 mg, 15.45 mmol) in dioxane (30 mL) at 0° C. was treated with 3-buten-1-ol (1.33 mL, 15.45 mmol), stirred for 2 hours, treated with 2-amino-6-chloropyrazine (1 g, 7.72 mmol), stirred at 100° C. for 2.5 days, cooled to room temperature, and diluted with ethyl acetate. The mixture was washed with water, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography eluting with hexanes/ethyl acetate (2:1) to provide the desired product (390 mg, 31%). MS (DCI/NH3) m/z 166.12 (M+H)+; 1H NMR (500 MHz, benzene-d6) δ 2.66 (m, 2H), 4.42 (t, J=6.87 Hz, 2H), 5.24 (dd, J=10.22, 1.98 Hz, 1H), 5.30 (m, 1H), 6.04 (m, 1H), 7.64 (s, 1H), 7.65 (s, 1H).

Workup

  1. stirringstirred at 100° C. for 2.5 days
  2. washThe mixture was washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography
  7. washeluting with hexanes/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-5cc36391fca446c9b030cfa3040ef63f
Source dataset
uspto-grants-2007_01
Patent number
US07163939B2

Reaction notes

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