Water → 6-Chloro-3-morpholinopyrido[2,3-b]pyrazine

HRID 509652Notes

Reaction equation

HRID 509652 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]=[C:9]([Cl:12])[CH:10]=[CH:11][C:5]2=[N:4][CH:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(N(CC)CC)C.O>C(Cl)Cl>[Cl:12][C:9]1[CH:10]=[CH:11][C:5]2[C:6]([N:8]=1)=[N:7][C:2]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[CH:3][N:4]=2

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 8471TriethylamineHCID 866975633,6-Dichloropyrido[2,3-b]pyrazine

Product 1

HCID 866975646-Chloro-3-morpholinopyrido[2,3-b]pyrazineYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3,6-dichloropyrido[2,3-b]pyrazine (E-28) (201 mg, 1 mmol, 1.0 eq) and morpholine (175 μL, 2 mmol, 2.0 eq) and triethylamine (270 μL, 2 mmol, 2.0 eq) in DCM (20 mL) was stirred at RT for 2 h. Then water (20 mL) was added. The organic layer was separated, washed with brine (2×10 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo to afford the desired product 6-chloro-3-morpholinopyrido[2,3-b]pyrazine (E-29) (100 mg, 40% yield). 1H NMR (300 MHz, CDCl3-d6) δ: 8.59 (s, 1H), 8.15 (d, J=6.6 Hz, 1H), 7.35 (d, J=6.3 Hz, 1H), 3.90 (m, 8H); ESI-MS m/z: 251.00 [M+H]+.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine (2×10 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-53ed30f20091457abca86dfc6d7d7a86
Source dataset
uspto-grants-2015_08
Patent number
US09096590B2

Reaction notes

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