Dipropylamine → HCID 58938695, compound

HRID 598062Notes

Reaction equation

[CH2:1]([N:8]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=2[CH3:24])=[C:15]2[C:10]([N:11]=[C:12](Cl)[N:13]([CH3:26])[C:14]2=[O:25])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([NH:31][CH2:32][CH2:33][CH3:34])[CH2:29][CH3:30]>O1CCOCC1>[CH2:1]([N:8]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=2[CH3:24])=[C:15]2[C:10]([N:11]=[C:12]([N:31]([CH2:32][CH2:33][CH3:34])[CH2:28][CH2:29][CH3:30])[N:13]([CH3:26])[C:14]2=[O:25])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution containing 0.089 g (0.23 mmol) of 2-benzyl-6-chloro-3-(2,4-dimethylphenyl)-5-methyl-2,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one in 15 ml of dioxane was added 0.06 ml (0.47 mmol) of dipropyl amine. The mixture was heated to 100° C. under a nitrogen atmosphere for 48 h. The reaction was concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with saturated sodium bicarbonate. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via biotage eluting with 40% ethyl acetate/hexanes gave 0.094 g (90.2%) of product.

Workup

concentrationThe reaction was concentrated under reduced pressure
dissolutionThe residue was dissolved in dichloromethane
washwashed with saturated sodium bicarbonate
dry with materialThe organic phase was dried over magnesium sulfate
filtrationFiltration, removal of solvent and purification of the residue via biotage
washeluting with 40% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-69e0866626234c3a8a89540c9bca4e20
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897607B2

Reaction notes

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