Methanol → 6-Bromo-4-(2-morpholinoethyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

HRID 1890835Notes

Reaction equation

HRID 1890835 reaction equation
Br[C:2]1[C:3]([NH:9][C:10](=[O:13])[CH2:11]I)=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.C(N(C(C)C)CC)(C)C.[O:23]1[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][NH2:31])[CH2:25][CH2:24]1.CO>C(#N)C.C(OCC)(=O)C>[Br:8][C:6]1[N:7]=[C:2]2[N:31]([CH2:30][CH2:29][N:26]3[CH2:27][CH2:28][O:23][CH2:24][CH2:25]3)[CH2:11][C:10](=[O:13])[NH:9][C:3]2=[N:4][CH:5]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 4082852-MorpholinoethylamineHCID 58298325N-(3,5-dibromopyrazin-2-yl)-2-iodoacetamide

Product 1

HCID 866446456-Bromo-4-(2-morpholinoethyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-oneYield 56.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
45 °C

Procedure

N-(3,5-Dibromopyrazin-2-yl)-2-iodoacetamide (0.5 g, 1.188 mmol), diisopropylethylamine (0.415 mL, 2.376 mmol) and 2-morpholinoethanamine (0.162 g, 1.248 mmol) were combined in acetonitrile (5 mL). The solution was heated to 45° C. for 1 h. Solution was condensed and diluted with 75% ethyl acetate in hexanes. The resulting solid was filtered and the filtrate collected and condensed followed by purification via Biotage chromatography (0-75% ethyl acetate in hexanes then 0-10% methanol in ethyl acetate) to afford the title compound (0.228 g, 0.67 mmol, 56% yield). MS (ESI) m/z 342.4 [M]+, 344.4 [M+2]+.

Workup

  1. customcondensed
  2. filtrationThe resulting solid was filtered
  3. customthe filtrate collected
  4. customcondensed
  5. customfollowed by purification via Biotage chromatography (0-75% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-eced75f2857e41fabfed45b5adcf1b59
Source dataset
uspto-grants-2013_08
Patent number
US08507492B2

Reaction notes

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