HCID 178524042, compound → HCID 178526515, compound

HRID 1592930Notes

Reaction equation

HRID 1592930 reaction equation
[OH:1][C:2]1[C:3]2[C:10](C(O)=O)=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1>N1C=CC=CC=1>[OH:1][C:2]1[C:3]2[CH:10]=[C:9]([C:14]3[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

3

Reactant 1

HCID 178524042HCID 178524042, compound

Product 1

HCID 178526515HCID 178526515, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
190 °C

Procedure

21 g of 4-hydroxy-6-(4-nitrophenyl)furo[2,3-d]pyrimidine-5-carboxylic acid are dissolved in ca. 200 ml of pyridine whilst heating, and subsequently concentrated by evaporation at 80° C. The residue is heated to 190° C. for 1 h, with a constant stream of nitrogen, in 500 ml of quinoline, which has been dried over magnesium sulfate, with 1 g of Cu2O (Aldrich, Buchs). The reaction mixture is allowed to cool and is added to 1 litre of 2.5 M hydrochloric acid, stirred and filtered by suction. The residue is washed with conc. ammonia solution and with H2O. The dark brown residue is dried in a HV: m.p.: >350° C.

Workup

  1. temperaturewhilst heating
  2. concentrationsubsequently concentrated by evaporation at 80° C
  3. dry with materialwhich has been dried over magnesium sulfate, with 1 g of Cu2O (Aldrich, Buchs)
  4. temperatureto cool
  5. additionis added to 1 litre of 2.5 M hydrochloric acid
  6. filtrationfiltered by suction
  7. washThe residue is washed with conc. ammonia solution and with H2O
  8. customThe dark brown residue is dried in a HV

Sources & evidence

ORD record
ord-0bf5bfa656d54239b01785f26a91602d
Source dataset
uspto-grants-2007_11
Patent number
US07294633B2

Reaction notes

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