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

HRID 1960870Notes

Reaction equation

HRID 1960870 reaction equation
C1COC2(N)N(C(NC3C=CC4OC(CO)=CC=4C=3)=NC=C2F)O1.[F:25][C:26]1[C:27]([NH:46][C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([OH:53])[CH:48]=2)=[N:28][C:29]([NH:32][C:33]2[CH:34]=[CH:35][C:36]3[O:40][C:39]([C:41](OC)=[O:42])=[CH:38][C:37]=3[CH:45]=2)=[N:30][CH:31]=1.CC(C[AlH]CC(C)C)C>>[F:25][C:26]1[C:27]([NH:46][C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([OH:53])[CH:48]=2)=[N:28][C:29]([NH:32][C:33]2[CH:34]=[CH:35][C:36]3[O:40][C:39]([CH2:41][OH:42])=[CH:38][C:37]=3[CH:45]=2)=[N:30][CH:31]=1

Participants

4

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 220602755-fluoro-N4-(3-hydroxyphenyl)-N2-(2-methoxycarbonylbenzofuran-5-yl)-2,4-pyrimidinediamineHCID 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)-N2-[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-0162a4079c084d41899c6a3281fa0ca5
Source dataset
uspto-grants-2013_04
Patent number
US08410266B2

Reaction notes

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