Diisopropylethylamine → 6-bromo-3,3-dimethyl-4-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

HRID 1047215Notes

Reaction equation

HRID 1047215 reaction equation
FC(F)(F)C(O)=O.Br[C:9]1[C:10]([NH:16][C:17](=[O:30])[C:18]([CH3:29])([NH:20][CH2:21][CH2:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH3:19])=[N:11][CH:12]=[C:13]([Br:15])[N:14]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1>[Br:15][C:13]1[N:14]=[C:9]2[N:20]([CH2:21][CH2:22][CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:18]([CH3:29])([CH3:19])[C:17](=[O:30])[NH:16][C:10]2=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 86696611N-(3,5-Dibromopyrazin-2-yl)-2-methyl-2-(2-(tetrahydro-2H-pyran-4-yl)ethylamino)propanamide trifluoroacetate

Product 1

HCID 533752276-bromo-3,3-dimethyl-4-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-oneYield 70.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

N-(3,5-Dibromopyrazin-2-yl)-2-methyl-2-(2-(tetrahydro-2H-pyran-4-yl)ethylamino)propanamide trifluoroacetate (0.856 g, 1.517 mmol), N,N-diisopropylethylamine (1.321 mL, 7.59 mmol) and 1,4-dioxane (25 mL) were combined in a sealable vessel with a stirbar. The system was purged with nitrogen and the resulting mixture was sealed, stirred vigorously and heated at 110° C. for 2.5 h. The reaction mixture was concentrated under reduced pressure and purified using flash chromatography (5-50% ethyl acetate in hexane) to give the desired product (0.394 g, 1.068 mmol, 70% yield) as a white solid. MS (ESI) m/z 369.4 [M]+, 371.3 [M+2]+.

Workup

  1. customThe system was purged with nitrogen
  2. customthe resulting mixture was sealed
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. custompurified

Sources & evidence

ORD record
ord-5fe2d895374840b388bea33e2e6893bf
Source dataset
uspto-grants-2013_10
Patent number
US08569494B2

Reaction notes

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