Tetrahydrofuran → HCID 22046287, compound

HRID 1830762Notes

Reaction equation

HRID 1830762 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 NaCl. 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) δ8.26 (s, H), 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 NaCl
  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-f14d55463ff54dcc9898813d05071f14
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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