Methanol → HCID 57897860, compound

HRID 1693541Notes

Reaction equation

HRID 1693541 reaction equation
[H-].[Na+].Br[C:4]1[N:5]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:6]2[N:7]=[C:8]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])[N:9]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[C:10](=[O:13])[C:11]=2[N:12]=1.[CH3:35][OH:36]>>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([N:9]2[C:10](=[O:13])[C:11]3[N:12]=[C:4]([O:36][CH3:35])[N:5]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:6]=3[N:7]=[C:8]2[C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 57897823HCID 57897823, compound

Product 1

HCID 57897860HCID 57897860, compound

Conditions

Temperature
80 °C

Procedure

A microwave tube is charged with sodium hydride (24.0 mg, 1.0 mmol) and dry methanol. After the reaction mixture is stirred for 3 min, 8-Bromo-1-(4-chloro-phenyl)-2-(2,4-dichloro-phenyl)-9-phenyl-1,9-dihydro-purin-6-one (8.0 mg, 0.015 mmol) is added. The tube is then capped and the mixture is heated in an oil bath for 3 h at 80° C. The reaction mixture is worked up by evaporating the solvent. The crude material is purified by flash chromatography. 1H NMR (CDCl3, 400 MHz) δ 7.63 (m, 4H), 7.43 (m, 1H), 7.28 (m, 4H), 7.11 (d, 2H), 7.03 (m, 1H), 4.25 (s, 3H). HPLC-MS calculated for C24H15Cl3N4O2 (M+H+) 497.0. Found: 497.0.

Workup

  1. customThe tube is then capped
  2. customby evaporating the solvent
  3. customThe crude material is purified by flash chromatography

Sources & evidence

ORD record
ord-7a36d5530f6a47fe8275260c9014ccfb
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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