2,5-Dimethoxytetrahydrofuran → HCID 13469429, compound

HRID 2290275Notes

Reaction equation

HRID 2290275 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[NH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.CO[CH:18]1[CH2:22][CH2:21][CH:20](OC)O1>C(O)(=O)C>[N:1]1([C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:9]([CH3:15])[NH:10][C:11](=[O:14])[NH:12][N:13]=3)=[CH:6][CH:7]=2)[CH:18]=[CH:22][CH:21]=[CH:20]1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 133860336-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

Product 1

HCID 13469429HCID 13469429, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 6-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (2.04 g) and 2,5-dimethoxytetrahydrofuran (1.32 g) in acetic acid (6 ml) was refluxed for 45 minutes and the allowed to stand at room temperature. The resultant precipitates were washed with diisopropyl ether and dissolved in a mixture of acetic acid, methanol and chloroform (1:2:50). The solution was chromatographed on silica gel (300 g) with a mixture of chloroform and methanol (10:1) as an eluent. The eluates were evaporated and the residue was crystallized from aqueous DMF to give 6-[4-(1-pyrrolyl)phenyl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (0.97 g).

Workup

  1. temperaturewas refluxed for 45 minutes
  2. customto stand at room temperature
  3. customThe resultant precipitates
  4. washwere washed with diisopropyl ether
  5. dissolutiondissolved in a mixture of acetic acid, methanol and chloroform (1:2:50)
  6. customThe solution was chromatographed on silica gel (300 g) with a mixture of chloroform and methanol (10:1) as an eluent
  7. customThe eluates were evaporated
  8. customthe residue was crystallized from aqueous DMF

Sources & evidence

ORD record
ord-5d65eb398e00476097c0db3b64098cdf
Source dataset
uspto-grants-1986_10
Patent number
US04616015

Reaction notes

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