Potassium Cyanide → HCID 57897926, compound

HRID 1693540Notes

Reaction equation

HRID 1693540 reaction equation
Br[C:2]1[N:3]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:4]2[N:5]=[C:6]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[N:7]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[C:8](=[O:11])[C:9]=2[N:10]=1.[C-:35]#[N:36].[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([N:7]2[C:8](=[O:11])[C:9]3[N:10]=[C:2]([C:35]#[N:36])[N:3]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:4]=3[N:5]=[C:6]2[C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:21][CH:20]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 57897912HCID 57897912, compound

Product 1

HCID 57897926HCID 57897926, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
200 °C

Procedure

8-Bromo-1-(4-chloro-phenyl)-9-phenyl-2-(4-trifluoromethyl-phenyl)-1,9-dihydro-purin-6-one (10.0 mg, 0.0183 mmol), potassium cyanide (110 mg, 1.68 mmol) and 18-crown-6 (12.0 mg, 0.0454 mmol) are added to a microwave tube with 1 mL of dry acetonitrile. The tube is capped and heated to 200° C. for 45 min in microwave reactor. The reaction mixture is then filtered and the filtrate is evaporated to dryness. The crude material is purified by column chromatography, yielding 6.2 mg (69%) of the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.64 (m, 5H), 7.52 (d, 2H), 7.38 (m, 4H), 7.12 (d, 2H). HPLC-MS calculated for C25H13ClF3N5O (M+H+) 492.1. Found: 492.1.

Workup

  1. customThe tube is capped
  2. filtrationThe reaction mixture is then filtered
  3. customthe filtrate is evaporated to dryness
  4. customThe crude material is purified by column chromatography

Sources & evidence

ORD record
ord-66212733751540edbf67061d4cd54a92
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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