Potassium Phosphate, Tribasic → HCID 89444312, compound

HRID 593209Notes

Reaction equation

HRID 593209 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:16])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[N:6][CH:7]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P([CH:38]2[CH2:43][CH2:42]CCC2)C2CCCCC2)CCCCC1.C1(B(O)O)CC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH:42]1([C:2]2[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:16])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[N:6][CH:7]=2)[CH2:43][CH2:38]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 89437205HCID 89437205, compound

Product 1

HCID 89444312HCID 89444312, compoundYield 11.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

In a sealed tube were added methyl 4-[(5-bromopyrazin-2-yl)amino]-4-oxo-butanoate (A2, 1.00 g, 3.47 mmol), K3PO4 (2.58 g), palladium (II) acetate (0.0795 g), tricyclohexyl phosphine (0.195 g), cyclopropylboronic acid (0.447 g), toluene (3 mL) and water (0.05 mL). Argon was bubbling through the mixture for ca. 5 min. The mixture was then heated under microwave irradiation for 5 min at 150° C. The mixture was diluted with ethyl acetate, washed with water and brine, dried and evaporated. The product was purified by flash chromatography (AcOEt/cyclohexane: 1/99→99/1) to give methyl 4-[(5-cyclopropylpyrazin-2-yl)amino]-4-oxo-butanoate (A31, 0.020 g, 0.080 mmol, 2.31% Yield). 1H NMR (400 MHz, CDCl3) 9.28 (1H, s), 8.24 (1H, s), 8.10 (1H, s), 3.72 (3H, s), 2.75-2.65 (4H, m), 2.00 (1H, m), 1.00 (4H, m).

Workup

  1. customArgon was bubbling through the mixture for ca. 5 min
  2. additionThe mixture was diluted with ethyl acetate
  3. washwashed with water and brine
  4. customdried
  5. customevaporated
  6. customThe product was purified by flash chromatography (AcOEt/cyclohexane: 1/99→99/1)

Sources & evidence

ORD record
ord-44e8ecc89e9948a4ac60b1862e9fa73f
Source dataset
uspto-grants-2016_01
Patent number
US09241489B2

Reaction notes

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