Phosphorus oxychloride → HCID 178515262, compound

HRID 408841Notes

Reaction equation

HRID 408841 reaction equation
O[C:2]1[N:3]([C:12]2[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[C:4](=[O:11])[C:5]2[N:6]=[CH:7][NH:8][C:9]=2[N:10]=1.P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:2]1[N:3]([C:12]2[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[C:4](=[O:11])[C:5]2[N:6]=[CH:7][NH:8][C:9]=2[N:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1785152632-Hydroxy-1-(6-chloropyridin-3-yl)-1,9-dihydro-6H-purin-6-one

Product 1

HCID 178515262HCID 178515262, compound

Conditions

Temperature
135 °C

Procedure

2-Hydroxy-1-(6-chloropyridin-3-yl)-1,9-dihydro-6H-purin-6-one from the above reaction is suspended in a large excess of phosphorous oxychloride (150 mL) and heated to 135° C. for 24 h. The reaction mixture is cooled, evaporated in vacuo, and additional toluene is added and evaporated (2×) under reduced pressure. The resulting sticky brown oil is dissolved in DCM (200 mL), and then neutralized with saturated NaHCO3 (aqueous). The aqueous layer is extracted with DCM (2×200 mL) and dried (MgSO4). The dried extract is filtered and concentrated under vacuum to afford crude product as a light brown solid. The crude product is purified by flash column chromatography using 1-2.5% MeOH/CH2Cl2 to afford the title compound as white solid. 1H NMR (300 MHz, CDCl3) δ 8.33 (s, 1H), 7.78 (s, 1H), 7.58 (d, J=6 Hz, 1H), 7.53 (d, J=6 Hz, 1H).

Workup

  1. temperatureThe reaction mixture is cooled
  2. customevaporated in vacuo, and additional toluene
  3. additionis added
  4. customevaporated (2×) under reduced pressure
  5. dissolutionThe resulting sticky brown oil is dissolved in DCM (200 mL)
  6. extractionThe aqueous layer is extracted with DCM (2×200 mL)
  7. dry with materialdried (MgSO4)
  8. extractionThe dried extract
  9. filtrationis filtered
  10. concentrationconcentrated under vacuum
  11. customto afford crude product as a light brown solid
  12. customThe crude product is purified by flash column chromatography

Sources & evidence

ORD record
ord-2426e61268434530a16ef08820220c0b
Source dataset
uspto-grants-2014_06
Patent number
US08759361B2

Reaction notes

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