Dichloromethane → HCID 58196525, compound

HRID 383672Notes

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.[CH2:13]([N:15]([CH2:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22])[CH2:16][CH3:17])[CH3:14].ClCCl>O1CCOCC1>[CH2:13]([N:15]([CH2:18][C:19]1[CH:20]=[C:21]([NH:22][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:23]=[CH:24][CH:25]=1)[CH2:16][CH3:17])[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-((diethylamino)methyl)aniline (148 mg, 0.829 mmol). The mixture was heated in microwave for 140 minutes at 120° C. Dichloromethane was added, and washed with water. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The resulting solution was prepared by TLC (10% MeOH/DCM) to yield 10 mg 5-(3-((diethylamino)methyl)phenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (11% yield). LCMS (M+1=324)

Workup

washwashed with water
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated under reduced pressure
customThe resulting solution was prepared by TLC (10% MeOH/DCM)

Sources & evidence

ORD record: ord-4354d4cf53774fcf9fad52f3eb8c590c
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367681B2

Reaction notes

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