Benzophenone imine → Benzhydrylidene-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-amine

HRID 403489Notes

Reaction equation

[C:1]1([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[NH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+].Br[C:68]1[CH:87]=[CH:86][C:71]([CH2:72][C:73]2[C:74]([CH2:84][CH3:85])=[N:75][N:76]3[C:81]([CH3:82])=[CH:80][C:79]([CH3:83])=[N:78][C:77]=23)=[CH:70][CH:69]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[C:7](=[N:8][C:68]1[CH:87]=[CH:86][C:71]([CH2:72][C:73]2[C:74]([CH2:84][CH3:85])=[N:75][N:76]3[C:81]([CH3:82])=[CH:80][C:79]([CH3:83])=[N:78][C:77]=23)=[CH:70][CH:69]=1)([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 105 °C

Procedure

Diphenylmethanimine (7.53 g, 39.5 mmol), BINAP (447 mg, 0.718 mmol) and sodium tert-butoxide (6.9 g, 71.8 mmol) were dissolved in 100 ml of toluene. The reaction mixture was heated to 105° C. and stirred for 5 min. Then 3-(4-bromo-benzyl)-2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidine (3) (13 g, 35.9 mmol) and palladium diacetate (81 mg, 0.36 mmol) were added and the reaction mixture was stirred for 12 h at 110° C. The organic layer was extracted two times with EtOAc, washed with water and brine, dried over Na2 SO4 and concentrated under reduced pressure. The precipitate was suspended in cyclohexane and filtered to afford a beige solid.

Workup

stirringthe reaction mixture was stirred for 12 h at 110° C
extractionThe organic layer was extracted two times with EtOAc
washwashed with water and brine
customdried over Na2 SO4
concentrationconcentrated under reduced pressure
filtrationfiltered
customto afford a beige solid

Sources & evidence

ORD record: ord-42e29716b9e84fa9b9a7884c95b1a570
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748435B2

Reaction notes

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