3-Chloroaniline → 5-(3-Chlorophenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

HRID 383686Notes

Reaction equation

HRID 383686 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([CH:11]=[O:12])=[C:4]2[N:3]=1.[Cl:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17]>O1CCOCC1>[Cl:13][C:14]1[CH:15]=[C:16]([NH:17][C:2]2[CH:7]=[CH:6][N:5]3[N:8]=[CH:9][C:10]([CH:11]=[O:12])=[C:4]3[N:3]=2)[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 581964015-Chloropyrazolo(1,5-a)pyrimidine-3-carbaldehyde

Product 1

HCID 581965285-(3-Chlorophenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To 5-chloropyrazolo[1,5-a]pyrimidine-3-carbaldehyde (120 mg, 0.66 mmol) in 1.5 mL dioxane was added 3-chloroaniline (351 μL, 3.31 mmol). The mixture was heated in microwave 10 minutes at 120° C. The solid formed was isolated by filtration and air dried to give 5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde as orange solid. LCMS (M+1=273)

Workup

  1. customThe solid formed
  2. customwas isolated by filtration and air
  3. customdried

Sources & evidence

ORD record
ord-42781197ba1b41f19dcf8b71354d1c01
Source dataset
uspto-grants-2013_02
Patent number
US08367681B2

Reaction notes

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