5-Aminoisoquinoline → N-(6-chloro-4-pyrimidinyl)-5-Isoquinolinamine

HRID 2117333Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[CH:9]1[C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([NH2:19])[C:13]=2[CH:12]=[CH:11][N:10]=1.CC(C)([O-])C.[Na+]>CC1C=CC(C)=CC=1>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:19][C:14]2[C:13]3[CH:12]=[CH:11][N:10]=[CH:9][C:18]=3[CH:17]=[CH:16][CH:15]=2)[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4,6-dichloropyrimidine (5 g, 34 mmol), isoquinolin-5-amine (5.3 g, 37 mmol), 2′-(dimethylamino)-2-biphenylyl palladium (II) chloride dinorbornylphosphine complex. [see Angew. Chem., 2002, 41, 3668; CAS number 359803-53-5] (940 mg, 2 mmol) and sodium tert-butoxide (4.8 g, 50 mmol) in p-xylene (100 ml) was degassed thoroughly and heated under nitrogen at 100° C. for 16 hours. The cooled reaction mixture was purified by column chromatography over silica (eluant 1% MeOH in DCM) to give the title compound (1.5 g, 17%).

Workup

customThe cooled reaction mixture
customwas purified by column chromatography over silica (eluant 1% MeOH in DCM)

Sources & evidence

ORD record: ord-32bc23fb4c03492a8057631fa57b4c91
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442701B2

Reaction notes

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