Diisobutylaluminum hydride → 7-Iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

HRID 1818992Notes

Reaction equation

[I:1][C:2]1[CH:12]=[N:11][C:5]2[NH:6][CH2:7][C:8](=O)[NH:9][C:4]=2[CH:3]=1.CC(C[AlH]CC(C)C)C>>[I:1][C:2]1[CH:12]=[N:11][C:5]2[NH:6][CH2:7][CH2:8][NH:9][C:4]=2[CH:3]=1

Participants

Reactant 2

HCID 14487Diisobutylaluminum hydride

HCID 448291147-iodo-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one

Product 1

HCID 578861297-Iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazineYield 31%

Procedure

7-Iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one (200 mg) was reduced as in General Procedure 3 using 4 eq DIBAL-H to give the title compound as a white solid (31% yield). M.p. 126-128° C., LCMS: m/z=262.30 (M+H+), 1H-NMR (DMSO-d6, 400 MHz) δ 3.13-3.17 (m, 2H), 3.27-3.29 (m, 2H), 5.78 (s, 1H), 6.37 (s, 1H), 6.78 (d, J=2.0 Hz, 1H), 7.33 (d, J=2.0 Hz, 1H).

Sources & evidence

ORD record: ord-b035d972d14c464984e77c897585df09
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601716B2

Reaction notes

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