Phosphorus oxychloride → 2-Chloro-1-propyl-8-[6-(3-trifluoromethyl-benzylamino)-pyridin-3-yl]-1,7-dihydro-purin-6-one

HRID 925559Notes

Reaction equation

HRID 925559 reaction equation
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[NH:10][C:9]([C:14]3[CH:15]=[N:16][C:17]([NH:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=4)=[CH:18][CH:19]=3)=[N:8][C:7]=2[NH:6][C:5]1=O)[CH2:2][CH3:3].O=P(Cl)(Cl)[Cl:35].[NH4+].[Cl-]>>[Cl:35][C:5]1[N:4]([CH2:1][CH2:2][CH3:3])[C:12](=[O:13])[C:11]2[NH:10][C:9]([C:14]3[CH:15]=[N:16][C:17]([NH:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=4)=[CH:18][CH:19]=3)=[N:8][C:7]=2[N:6]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 25517Ammonium ChlorideHCID 674976141-Propyl-8-[6-(3-trifluoromethyl-benzylamino)-pyridin-3-yl]-3,7-dihydro-purine-2,6-dione

Product 1

HCID 674981072-Chloro-1-propyl-8-[6-(3-trifluoromethyl-benzylamino)-pyridin-3-yl]-1,7-dihydro-purin-6-oneYield 26%

Conditions

Temperature
127.5 °C

Procedure

A mixture of 1-Propyl-8-[6-(3-trifluoromethyl-benzylamino)-pyridin-3-yl]-3,7-dihydro-purine-2,6-dione (0.2 g, 0.45 mmol), POCl3 (5 ml) and NH4Cl (0.486 g, 9 mmol) were heated at 125-130° C. for 20 hours. Reaction mixture was cooled to 20-25° C. It was then concentrated under vacuum. The residue was dissolved in water (50 ml) and precipitated solid was filtered off. The solid obtained was further purified by column chromatography to obtain pure 2-Chloro-1-propyl-8-[6-(3-trifluoromethyl-benzylamino)-pyridin-3-yl]-1,7-dihydro-purin-6-one as pale yellow solid (0.054 g, 26%).

Workup

  1. customReaction mixture
  2. temperaturewas cooled to 20-25° C
  3. concentrationIt was then concentrated under vacuum
  4. dissolutionThe residue was dissolved in water (50 ml)
  5. customprecipitated solid
  6. filtrationwas filtered off
  7. customThe solid obtained
  8. customwas further purified by column chromatography

Sources & evidence

ORD record
ord-16774ad2272145438553496305f1ba1f
Source dataset
uspto-grants-2016_03
Patent number
US09284316B2

Reaction notes

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