Potassium Hydroxide → 2-Morpholin-4-yl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine

HRID 1713142Notes

Reaction equation

HRID 1713142 reaction equation
[N:1]1([C:7]2[N:8]=[C:9]3[CH2:16][CH2:15][N:14](C(OCC)=O)[CH2:13][C:10]3=[N:11][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].[K+]>CO.O>[N:1]1([C:7]2[N:8]=[C:9]3[CH2:16][CH2:15][NH:14][CH2:13][C:10]3=[N:11][CH:12]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59463563Ethyl 2-morpholin-4-yl-7,8-dihydropyrido[3,4-b]pyrazine-6(5H)-carboxylate

Product 1

HCID 574205822-Morpholin-4-yl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 2-morpholin-4-yl-7,8-dihydropyrido[3,4-b]pyrazine-6(5H)-carboxylate (105 mg, 0.359 mmol) is dissolved in MeOH (5 mL) and H2O (5 mL). KOH (1.00 g, 17.9 mmol) is added, and the reaction mixture is stirred overnight at 50° C. The mixture is cooled and partitioned between brine (50 mL) and DCM (50 mL). The mixture is extracted with DCM (2×50 mL). The combined organic extracts are dried and evaporated to yield the title compound. MS (+VE) m/z 221.21 (M++1).

Workup

  1. temperatureThe mixture is cooled
  2. custompartitioned between brine (50 mL) and DCM (50 mL)
  3. extractionThe mixture is extracted with DCM (2×50 mL)
  4. customThe combined organic extracts are dried
  5. customevaporated

Sources & evidence

ORD record
ord-b4740e0224bf4ec8a7f3846fe49d9db8
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

Loading…