3-(Propan-2-yloxy)aniline → 5-(3-Isopropoxyphenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

HRID 383680Notes

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.[CH:13]([O:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20])([CH3:15])[CH3:14]>O1CCOCC1>[CH:13]([O:16][C:17]1[CH:18]=[C:19]([NH:20][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:21]=[CH:22][CH:23]=1)([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 120 °C

Procedure

To 5-chloropyrazolo[1,5-a]pyrimidine-3-carbaldehyde (50 mg, 0.276 mmol) in dioxane was added 3-isopropoxyaniline (125 mg, 0.829 mmol). The mixture was heated in microwave for 20 minutes at 120° C. The solid produced was isolated by filtration and then purified by preparative TLC (2% MeOH/DCM) to yield 5-(3-isopropoxyphenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde. LCMS (M+1=297)

Workup

customThe solid produced
customwas isolated by filtration
custompurified by preparative TLC (2% MeOH/DCM)

Sources & evidence

ORD record: ord-0943c62de7e54027beef998dc3b3cde0
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367681B2

Reaction notes

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