Diisobutylaluminum hydride → 5-fluoro-N2-[2-(hydroxymethyl)benzofuran-5-yl]-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine

HRID 405553Notes

Reaction equation

HRID 405553 reaction equation
C1CO[C:8]2([NH2:9])[N:3]([C:4]([NH:13][C:14]3[CH:15]=[CH:16][C:17]4[O:21][C:20]([CH2:22][OH:23])=[CH:19][C:18]=4[CH:24]=3)=[N:5][CH:6]=[C:7]2[F:12])O1.CC(C[AlH]C[CH:31]([CH3:33])[CH3:32])C>>[F:12][C:7]1[C:8]([NH:9][C:32]2[CH:31]=[CH:33][CH:22]=[C:20]([OH:21])[CH:19]=2)=[N:3][C:4]([NH:13][C:14]2[CH:15]=[CH:16][C:17]3[O:21][C:20]([CH2:22][OH:23])=[CH:19][C:18]=3[CH:24]=2)=[N:5][CH:6]=1

Participants

3

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 66759177N4-(3,4-ethylenedioxy)-5-fluoro-N2-[2-(hydroxymethyl)benzofuran-5-yl]-2,4-pyrimidinediamine

Product 1

HCID 220604395-fluoro-N2-[2-(hydroxymethyl)benzofuran-5-yl]-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine

Procedure

In a manner similar to the preparation of N4-(3,4-ethylenedioxy)-5-fluoro-N2-[2-(hydroxymethyl)benzofuran-5-yl]-2,4-pyrimidinediamine, 5-fluoro-N4-(3-hydroxyphenyl)-N-2-[2-(methoxycarbonyl)benzofuran-5-yl]-2,4-pyrimidinediamine was reduced with DIBALH to yield 5-fluoro-N2-[2-(hydroxymethyl)benzofuran-5-yl]-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.37 (s, 1H), 9.17 (s, 1H), 9.12 (s, 1H), 8.06 (d, 1H, J=3.9 Hz), 8.01 (d, 1H, J=1.8 Hz), 7.41-7.35 (m, 2H), 7.26 (d, 1H, J=8.1 Hz), 7.11-7.05 (m, 2H), 6.60 (s, 1H), 6.51 (dd, 1H, J=2.4 and 8.4 Hz), 5.41 (t, 1H, J=6.0 Hz), 4.51 (d, 2H, J=5.7 Hz); LCMS: ret. time: 16.21 min.; purity: 95%; MS (m/e): 367 (MH+).

Sources & evidence

ORD record
ord-3b62dcd1420a4dc7b90828c6d53f3774
Source dataset
uspto-grants-2014_06
Patent number
US08748597B2

Reaction notes

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