Water → 1-Methyl-1H-pyrazolo[3',4':4,5]thieno[2,3-b]pyridin-3-amine

HRID 27234Notes

Reaction equation

HRID 27234 reaction equation
[C:1]([C:3]1[S:11][C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[C:4]=1Cl)#[N:2].[CH3:13][NH:14][NH2:15].O>CS(C)=O>[CH3:13][N:14]1[C:4]2[C:5]3[C:6]([S:11][C:3]=2[C:1]([NH2:2])=[N:15]1)=[N:7][CH:8]=[CH:9][CH:10]=3

Participants

5

Reactant 3

HCID 962WaterHCID 6061MethylhydrazineHCID 233442793-Chlorothieno[2,3-b]pyridine-2-carbonitrile

Product 1

HCID 233442801-Methyl-1H-pyrazolo[3',4':4,5]thieno[2,3-b]pyridin-3-amineYield 81.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

15 Grams (0.066 mole) of 2-cyano-3-chlorothieno (2,3-b)pyridine and 17.5 ml (0.33 mole) of methylhydrazine were dissolved in 110 ml of dimethylsulfoxide and heated to 75° for 15 hr under nitrogen. The reaction was cooled and poured into water. The solid was filtered and dried to give 11 g of 1-methyl-1H-pyrazolo(3',4':4,5)thieno(2,3-b)pyridine-3-amine. m.p. 194°-196° C. NMR(CDCl3) δ4.0(s,3); 5.2(s,2); 7.4(dd,1); 8.4(m,2).

Workup

  1. temperatureheated to 75° for 15 hr under nitrogen
  2. temperatureThe reaction was cooled
  3. filtrationThe solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-7c5b9901ca86485e831d108c21cb3395
Source dataset
uspto-grants-1980_09
Patent number
US04220776

Reaction notes

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