Dimethylformamide → HCID 178462996, compound

HRID 460754Notes

Reaction equation

HRID 460754 reaction equation
C(O[C:4]([C:6]1[C:7](Cl)=[C:8]2[CH:14]=[N:13][N:12]([CH2:15][CH3:16])[C:9]2=[N:10][CH:11]=1)=[O:5])C.[NH2:18][C:19]1[NH:23][N:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.CN(C)C=O>O>[CH2:15]([N:12]1[C:9]2[N:10]=[CH:11][C:6]3[C:4](=[O:5])[N:23]4[N:22]=[CH:21][CH:20]=[C:19]4[NH:18][C:7]=3[C:8]=2[CH:14]=[N:13]1)[CH3:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 74561Pyrazol-3-ylamineHCID 10491120ethyl 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Product 1

HCID 178462996HCID 178462996, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

126 g. of 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (0.5 mol.), 41.5 g. of 5-amino-pyrazole (0.5 mol.) and 50.6 g. of triethylamine (0.5 mol.) are heated at reflux temperature with stirring in 250 ml. of dimethylformamide for 16 hours. After cooling, about 300 ml. of water are added and the white precipitated product, 3-ethyl-3,11-dihydro-6H-pyrazolo[1,5-a]pyrazolo-[4',3':5,6]pyrido[4,3-d]pyrimidin-6-one is filtered off, yield 57.7 g (45.4%); m.p. >300° (DMF).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. filtrationthe white precipitated product, 3-ethyl-3,11-dihydro-6H-pyrazolo[1,5-a]pyrazolo-[4',3':5,6]pyrido[4,3-d]pyrimidin-6-one is filtered off

Sources & evidence

ORD record
ord-b7a3c71df28144f1a1522477660493e2
Source dataset
uspto-grants-1977_12
Patent number
US04061632

Reaction notes

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