Diphenyl Ether → HCID 178469574, compound

HRID 1833333Notes

Reaction equation

HRID 1833333 reaction equation
[CH3:1][C:2]1[CH:22]=[C:5]2[N:6]=[C:7]([CH3:21])[CH:8]=[C:9]([NH:10][CH:11]=[C:12]([C:18]([O-:20])=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:4]2[N:3]=1.C1(OC2C=CC=CC=2)C=CC=CC=1>C(OCC)C>[OH:20][C:18]1[C:8]2[C:7]([CH3:21])=[N:6][C:5]3[N:4]([N:3]=[C:2]([CH3:1])[CH:22]=3)[C:9]=2[N:10]=[CH:11][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 86735320HCID 86735320, compound

Product 1

HCID 178469574HCID 178469574, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

33.2 g. of [[(2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl)amino]methylene]propanedioic acid, ethyl ester (0.1 mol.) are heated in 100 ml. of diphenyl ether at 240° for 7 minutes. The mixture is cooled rapidly and 100 ml. of diethyl ether are added. The product, 6-hydroxy-2,5-dimethylpyrazolo[1,5-a]pyrido[3,2-e]pyrimidine-7-carboxylic acid, ethyl ester, precipitates and is filtered off, yield 20.1 g. (75%), m.p. 207°-208° (methanol).

Workup

  1. temperatureThe mixture is cooled rapidly
  2. customThe product, 6-hydroxy-2,5-dimethylpyrazolo[1,5-a]pyrido[3,2-e]pyrimidine-7-carboxylic acid, ethyl ester, precipitates
  3. filtrationis filtered off

Sources & evidence

ORD record
ord-f5a87620302e49ad970493b3a49bf119
Source dataset
uspto-grants-1978_01
Patent number
US04066644

Reaction notes

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