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

HRID 2361210Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]2[N:11]([CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH2:10][C:9](=[O:20])[NH:8][C:5]2=[N:6][CH:7]=1.BrC1C(N[C:30](=[O:33])[CH2:31]I)=NC=C(Br)N=1.C(N([CH:40]([CH3:42])[CH3:41])CC)(C)C.O1CCN(CCN)C[CH2:44]1.[C:52](#[N:54])[CH3:53]>C(OCC)(=O)C.CO>[OH:33][C:30]([C:42]1[N:54]=[CH:52][C:53]([C:2]2[N:3]=[C:4]3[N:11]([CH2:12][CH2:13][N:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)[CH2:10][C:9](=[O:20])[NH:8][C:5]3=[N:6][CH:7]=2)=[CH:41][CH:40]=1)([CH3:44])[CH3:31]

Participants

Conditions

Temperature: 45 °C

Procedure

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

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

Sources & evidence

ORD record: ord-e12222234a22466abf40c3909b74ce05
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686135B2

Reaction notes

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