Water → HCID 58313837, compound

HRID 624809Notes

Reaction equation

HRID 624809 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)[N:5]2[N:12]=[CH:13][C:14]([CH:15]=[O:16])=[C:4]2[N:3]=1.[CH3:17][S-:18].[Na+].O>CN(C)C=O>[CH:9]1([NH:8][C:6]2[N:5]3[N:12]=[CH:13][C:14]([CH:15]=[O:16])=[C:4]3[N:3]=[C:2]([S:18][CH3:17])[CH:7]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 581966475-Chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

Product 1

HCID 58313837HCID 58313837, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (4.0 g, 16.87 mmol) in dimethylformamide was added sodium thiomethoxide (3.54 g, 50.5 mmol) and the reaction mixture was heated to 80° C. for 2 hrs. Cooled the reaction mixture, added water, stirred for 15 minutes and filtered white precipitate, dried to yield 7-(cyclopropylamino)-5-(methylthio)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (3.60 g, 86% yield). LCMS (M+1=249)

Workup

  1. temperatureCooled the reaction mixture
  2. filtrationfiltered white precipitate
  3. customdried

Sources & evidence

ORD record
ord-14ff3fceb51b40e2912e86af90b7b7cd
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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