Triethylamine → 6-(6-(1-(Tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)pyridin-3-yl)-4-(tetrahydro-2H-pyran-4-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

HRID 717164Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([Sn](C)(C)C)[N:15]=3)[NH:10][C:9](=[O:21])[CH2:8]2)[CH2:3][CH2:2]1.Br[C:23]1[CH:24]=[CH:25][C:26]([C:29]2[N:33]=[CH:32][N:31]([CH:34]3[CH2:39][CH2:38][CH2:37][CH2:36][O:35]3)[N:30]=2)=[N:27][CH:28]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN(C)C=O>[O:35]1[CH2:36][CH2:37][CH2:38][CH2:39][CH:34]1[N:31]1[CH:32]=[N:33][C:29]([C:26]2[N:27]=[CH:28][C:23]([C:14]3[N:15]=[C:16]4[N:7]([CH:4]5[CH2:5][CH2:6][O:1][CH2:2][CH2:3]5)[CH2:8][C:9](=[O:21])[NH:10][C:11]4=[N:12][CH:13]=3)=[CH:24][CH:25]=2)=[N:30]1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 4-(tetrahydro-2H-pyran-4-yl)-6-(trimethylstannyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one (1 equiv), 5-bromo-2-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)pyridine (1.2 equiv), tris(dibenzylideneacetone)dipalladium (0.1 equiv), tri-o-tolylphosphine (0.2 equiv), triethylamine (3 equiv) and N,N-dimethylformamide was heated at 95° C. for 3 h under nitrogen. Concentration and chromatography purification give the desired product in 39% yield. MS (ESI) m/z 463.1 [M+1]+.

Workup

concentrationConcentration and chromatography purification

Sources & evidence

ORD record: ord-415a708e2786460aaf8ba07c61bcb191
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193692B2

Reaction notes

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