Diisobutylaluminum hydride → HCID 22060456, compound

HRID 1163653Notes

Reaction equation

C([O:3][C:4]([C:6]([CH3:33])([CH3:32])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[C:19]([F:20])=[CH:18][N:17]=[C:16]([NH:21][C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][CH2:30][O:31][C:24]=4[CH:23]=3)[N:15]=2)=[CH:9][CH:8]=1)=O)C.CC(C[AlH]CC(C)C)C>>[CH2:30]1[CH2:29][O:28][C:25]2[CH:26]=[CH:27][C:22]([NH:21][C:16]3[N:15]=[C:14]([NH:13][C:10]4[CH:11]=[CH:12][C:7]([C:6]([CH3:32])([CH3:33])[CH2:4][OH:3])=[CH:8][CH:9]=4)[C:19]([F:20])=[CH:18][N:17]=3)=[CH:23][C:24]=2[O:31]1

Participants

Reactant 2

HCID 14487Diisobutylaluminum hydride

HCID 22060321HCID 22060321, compound

Product 1

HCID 22060456HCID 22060456, compound

Procedure

In like manner to the preparation of N2-(3,4-ethylenedioxyphenyl)-5-fluoro-N4-[4(2-hydroxy-1,1-dimethylethyl)phenyl]-pyrimidine-2,4-diamine, N4-[4-[ethoxycarbonyl(dimethyl)methyl]phenyl]-N2-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine was reduced with DIBALH to give N2-(3,4-ethylenedioxyphenyl)-5-fluoro-N4-[4-(2-hydroxy-1,1-dimethylethyl)phenyl]-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.23 (s, 1H), 8.94 (s, 1H), 8.01 (d, 1H, J=3.5 Hz), 7.63 (d, 2H, J=8.8 Hz), 7.31-7.27 (m, 3H), 6.98 (dd, 1H, J=2.9 and 8.8 Hz), 6.65 (d, 1H, J=8.8 Hz), 4.65 (t, 1H, J=5.3 Hz), 4.17-4.16 (m, 4H), 3.39 (d, 2H, J=5.2 Hz), 1.20 (s, 6H). 8.9 Hz), LCMS: ret. time: 19.52 min.; purity: 100%; MS (m/e): 411 (MH+).

Sources & evidence

ORD record: ord-5b4f4b2dad8947feb116485244130d12
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820819B2

Reaction notes

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