alpha-Methyl-3-pyridinemethanol → 3-(6-chloro-8-oxo-9-(1-(pyridin-3-yl)ethyl)-8,9-dihydro-7H-purin-2-yl)-3H-benzo[d]imidazole-5-carbonitrile

HRID 600441

Reaction equation

HRID 600441 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7](O)[CH3:8])[CH:2]=1.[Cl:10][C:11]1[N:19]=[C:18]([N:20]2[C:24]3[CH:25]=[C:26]([C:29]#[N:30])[CH:27]=[CH:28][C:23]=3[N:22]=[CH:21]2)[N:17]=[C:16]2[C:12]=1[NH:13][C:14](=[O:31])[NH:15]2>>[Cl:10][C:11]1[N:19]=[C:18]([N:20]2[C:24]3[CH:25]=[C:26]([C:29]#[N:30])[CH:27]=[CH:28][C:23]=3[N:22]=[CH:21]2)[N:17]=[C:16]2[C:12]=1[NH:13][C:14](=[O:31])[N:15]2[CH:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH3:8]

Participants

3

Reactant 2

HCID 101192alpha-Methyl-3-pyridinemethanolHCID 576127423-(6-chloro-8-oxo-8,9-dihydro-7H-purin-2-yl)-3H-benzo[d]imidazole-5-carbonitrile

Product 1

HCID 576127403-(6-chloro-8-oxo-9-(1-(pyridin-3-yl)ethyl)-8,9-dihydro-7H-purin-2-yl)-3H-benzo[d]imidazole-5-carbonitrileYield 26%

Procedure

Yellow oil (26% yield based on 73% conversion). Synthesized using 1-pyridin-3-yl-ethanol and 3-(6-chloro-8-oxo-8,9-dihydro-7H-purin-2-yl)-3H-benzo[d]imidazole-5-carbonitrile. 1H NMR (300 MHz, CD3OD) δ, ppm: 9.27 (s, 1H), 9.20-9.00 (br m, 1H), 8.86 (d, 1H), 8.88-8.77 (m, 1H, overlapping with 8.86 ppm), 8.68 (s, 1H), 8.13 (br s, 1H), 7.87 (d, 1H), 7.68 (d, 1H), 6.17 (q, J=7.1 Hz, 1H), 2.19 (d, J=7.3 Hz, 3H); MS (EI) m/z 417.1 (MH)+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-7cba0372b52e4a33b872b18f7ed08ea6
Source dataset
uspto-grants-2011_03
Patent number
US07902187B2

Linked notes

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