Acetonitrile → 6-(6-(2-Hydroxypropan-2-yl)pyridin-3-yl)-4-((tetrahydro-2H-pyran-4-yl)methyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

HRID 2361229Notes

Reaction equation

HRID 2361229 reaction equation
Br[C:2]1[N:3]=[C:4]2[N:11]([CH2:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH2:10][C:9](=[O:19])[NH:8][C:5]2=[N:6][CH:7]=1.BrC1C(N[C:29](=[O:32])[CH2:30]I)=NC=C(Br)N=1.O1CCC(CN)C[CH2:34]1.C(N([CH:47]([CH3:49])[CH3:48])CC)(C)C.[C:50](#[N:52])[CH3:51]>>[OH:32][C:29]([C:49]1[N:52]=[CH:50][C:51]([C:2]2[N:3]=[C:4]3[N:11]([CH2:12][CH:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)[CH2:10][C:9](=[O:19])[NH:8][C:5]3=[N:6][CH:7]=2)=[CH:48][CH:47]=1)([CH3:34])[CH3:30]

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 27732104-AminomethyltetrahydropyranHCID 58298325N-(3,5-dibromopyrazin-2-yl)-2-iodoacetamideHCID 715670846-Bromo-4-((tetrahydro-2H-pyran-4-yl)methyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

Product 1

HCID 582983126-(6-(2-Hydroxypropan-2-yl)pyridin-3-yl)-4-((tetrahydro-2H-pyran-4-yl)methyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-oneYield 79%

Conditions

Temperature
40 °C

Procedure

6-Bromo-4-((tetrahydro-2H-pyran-4-yl)methyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one. N-(3,5-Dibromopyrazin-2-yl)-2-iodoacetamide (See Example 5.B) (8.0 g, 19.01 mmol), (tetrahydro-2H-pyran-4-yl)methanamine (2.63 g, 22.81 mmol) and diisopropylethylamine (6.64 mL, 38.0 mmol) were placed in a 250 mL round bottom flask, suspended in acetonitrile (80.0 mL) and heated to 40° C. for 16 h. The resulting white precipitate was filtered, washed with acetonitrile followed by hexanes and dried under vacuum to afford the title compound (4.89 g, 14.95 mmol, 79% yield). MS (ESI) m/z 327.4 [M]+, 329.5 [M+2]+.

Workup

  1. filtrationThe resulting white precipitate was filtered
  2. washwashed with acetonitrile
  3. customdried under vacuum

Sources & evidence

ORD record
ord-4707464a3c7a42aa9db4a242abb62d2b
Source dataset
uspto-grants-2014_04
Patent number
US08686135B2

Reaction notes

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