Tetrahydrofuran → HCID 22046287, compound

HRID 1821778Notes

Reaction equation

HRID 1821778 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.C[Mg]I.[N-:12]=[C:13]=[O:14].[CH2:15]1[CH2:19][O:18][CH2:17][CH2:16]1>>[Cl:8][C:4]1[N:3]=[C:2]([NH:1][C:13]([NH:12][C:15]2[CH:16]=[C:16]([CH3:17])[CH:15]=[CH:19][C:19]=2[O:18][CH3:17])=[O:14])[CH:7]=[N:6][CH:5]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 105034IsocyanateHCID 1184582-Amino-6-ChloropyrazineHCID 178418373HCID 178418373, compound

Product 1

HCID 22046287HCID 22046287, compound

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-amino-6-chloropyrazine (130 mg, 1 mmol) in 3 mL THF at 0° C. under nitrogen was added methyl magnesium iodide (3M in Et2O, 330 μL, 1 mmol) to give a yellow suspension that was stirred at 0° C. for 15 minutes. The suspension was treated with the isocyanate neat (147 μL, 1 mmol) and allowed to warm to room temperature overnight. The reaction was partitioned between EtOAc (30 mL) and 10% Na2CO3 (30 mL). The organics were isolated and washed 1×30 mL with 10% Na2CO3 and 1×30 mL with saturated NaCI. The organics were dried (MgSO4), filtered and concentrated to a crude residue that was triturated with EtOAc to give, after filtration, the urea product as a white solid (27 mg, 9%). 1H-NMR (400 MHz, CDCl3) δ 8.26 (s, 1H), 8.23 (s, 1H), 8.17 (s, 1H), 8.09 (br s, 1H), 6.84 (d, 1H), 6.81 (d, 1H), 3.96 (s, 3H), 2.35 (s, 3H). LRMS (ESI, Positive) m/e 293.0 (M+1).

Workup

  1. customto give a yellow suspension that
  2. temperatureto warm to room temperature overnight
  3. customThe reaction was partitioned between EtOAc (30 mL) and 10% Na2CO3 (30 mL)
  4. customThe organics were isolated
  5. washwashed 1×30 mL with 10% Na2CO3 and 1×30 mL with saturated NaCI
  6. dry with materialThe organics were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated to a crude residue that
  9. customwas triturated with EtOAc
  10. customto give
  11. filtrationafter filtration

Sources & evidence

ORD record
ord-b563abe272fc4f418b5a3adac37ff36c
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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