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

HRID 1932183Notes

Reaction equation

HRID 1932183 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][C:50]([O:53][CH:54]([CH3:56])[CH3:55])=[CH:49][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][C:50]([O:53][CH:54]([CH3:56])[CH3:55])=[CH:49][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 220603265-fluoro-N2-(2-methoxycarbonylbenzofuran-5-yl)-N4-(4-isopropoxyphenyl)-2,4-pyrimidinediamineHCID 66759177N4-(3,4-ethylenedioxy)-5-fluoro-N2-[2-(hydroxymethyl)benzofuran-5-yl]-2,4-pyrimidinediamine

Product 1

HCID 220603615-fluoro-N2-[2-(hydroxymethyl)benzofuran-5-yl]-N4-(4-isopropoxyphenyl)-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-N2-(2-methoxycarbonylbenzofuran-5-yl)-N4-(4-isopropoxyphenyl)-2,4-pyrimidinediamine was reduced with DIBALH to yield 5-fluoro-N2-[2-(hydroxymethyl)benzofuran-5-yl]-N4-(4-isopropoxyphenyl)-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.83 (d, 1H, J=3.3 Hz), 7.81 (s, 1H), 7.50 (d, 2H, J=9.0 Hz), 7.29 (d, 1H, J=9.0 Hz), 7.22 (dd, 1H, J=2.4 and 8.7 Hz), 6.84 (d, 2H, J=8.7 Hz), 6.56 (d, 1H, J=1.2 Hz), 4.64 (s, 2H), 4.56 (2q, 1H, J=5.7 Hz), 1.31 (d, 6H, J=6.0 Hz); 19F NMR (CD3OD): −47926; LCMS: ret. time: 21.03 min.; purity: 99%; MS (m/e): 409 (MH+).

Sources & evidence

ORD record
ord-ca17f86aed004ad1a33dac23130669bf
Source dataset
uspto-grants-2012_05
Patent number
US08188276B2

Reaction notes

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