Tetrahydro-3-furanmethanol → HCID 24831491, compound

HRID 2074194Notes

Reaction equation

HRID 2074194 reaction equation
[F:1][C:2]1([F:27])[CH2:5][N:4]([C:6]2[N:14]=[C:13]([N:15]3[C:19]4[CH:20]=[C:21]([C:24]#[N:25])[CH:22]=[CH:23][C:18]=4[N:17]=[CH:16]3)[N:12]=[C:11]3[C:7]=2[NH:8][C:9](=[O:26])[NH:10]3)[CH2:3]1.[O:28]1[CH2:32][CH2:31][CH:30]([CH2:33]O)[CH2:29]1>C(Cl)(Cl)Cl>[F:27][C:2]1([F:1])[CH2:3][N:4]([C:6]2[N:14]=[C:13]([N:15]3[C:19]4[CH:20]=[C:21]([C:24]#[N:25])[CH:22]=[CH:23][C:18]=4[N:17]=[CH:16]3)[N:12]=[C:11]3[C:7]=2[NH:8][C:9](=[O:26])[N:10]3[CH2:33][CH:30]2[CH2:31][CH2:32][O:28][CH2:29]2)[CH2:5]1

Participants

4

Reactant 2

HCID 139980Tetrahydro-3-furanmethanolHCID 67059520HCID 67059520, compound

Product 1

HCID 24831491HCID 24831491, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

White solid. 18% yield. Synthesized from 3-(6-(3,3-difluoroazetidin-1-yl)-8-oxo-8,9-dihydro-7H-purin-2-yl)-3H-benzo[d]imidazole-5-carbonitrile (0.12 mmol) and tetrahydro-3-furan-methanol following the general procedure for diversifying at the N9 position of the purinones based on a Mitsunobu reaction. 1H NMR (300 MHz, CDCl3+CD3OD) δ, ppm: 9.22 (s, 1H), 8.99 (s, 1H), 7.89 (d, 1H), 7.67 (d, 1H), 4.76 (t, 4H), 4.10-3.97 (m, 3H), 3.90-3.77 (m, 3H), 3.06-2.93 (m, 1H), 2.22-2.07 (m, 1H), 1.90-1.83 (m, 1H); IR (CHCl3), cm−1: 2979 (w), 1703 (s), 1367 (m), 1167 (m); MS (EI) m/z 453.1 (MH)+.

Workup

  1. custombased on a Mitsunobu reaction

Sources & evidence

ORD record
ord-500aef5784454479b56c2d3aec1423e8
Source dataset
uspto-grants-2011_04
Patent number
US07919490B2

Reaction notes

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