3-(1,2,3,4-Tetrahydro-isoquinolin-5-yl)-pyridin-4-ylamine → 2-[5-(4-amino-pyridin-3-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-6,7-dimethoxy-3H-quinazolin-4-one

HRID 8737

Reaction equation

Cl[C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.[CH2:17]1[C:26]2[C:21](=[C:22]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][C:32]=3[NH2:33])[CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][NH:18]1>COC(O)C>[NH2:33][C:32]1[CH:31]=[CH:30][N:29]=[CH:28][C:27]=1[C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:21]=1[CH2:20][CH2:19][N:18]([C:2]1[NH:11][C:10](=[O:12])[C:9]3[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=3)[N:3]=1)[CH2:17]2

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one 1b (0.076 g, 0.31 mmol) and 3-(1,2,3,4-tetrahydro-isoquinolin-5-yl)-pyridin-4-ylamine (0.075 g, 0.33 mmol) in methoxyethanol (5 mL) was heated to 95° C. with stirring for 18 h the volatiles were evaporated and the residue was purified by flash column eluting with 2% methanol in dichloromethane containing 0.2% of ammonium hydroxide to yield 2-[5-(4-amino-pyridin-3-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-6,7-dimethoxy-3H-quinazolin-4-one 902. The product was converted to the hydrochloric acid salt, mp. >300° C., [M+H]+=430.

Workup

customwere evaporated
customthe residue was purified by flash column
washeluting with 2% methanol in dichloromethane containing 0.2% of ammonium hydroxide

Sources & evidence

ORD record: ord-f83e86f633f84f5f9939b049f416c75f
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091200B2

Linked notes

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