Propylamine → 5,6-Dimethyl-2-(propylamino)-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine hydrochloride

HRID 275907Notes

Reaction equation

[CH2:1]([NH2:4])[CH2:2][CH3:3].C(N(CC)CC)C.[Cl:12][C:13]1[N:18]=[C:17]([N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20]2)[C:16]([CH3:29])=[C:15]([CH3:30])[N:14]=1>CN(C)C=O.ClCCl>[ClH:12].[CH3:29][C:16]1[C:17]([N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20]2)=[N:18][C:13]([NH:4][CH2:1][CH2:2][CH3:3])=[N:14][C:15]=1[CH3:30]

Participants

Conditions

Temperature: 130 °C

Procedure

Propylamine(0.44 g, 5.4 mmol) and triethylamine(0.38 ml, 2.7 mmol) were added to a mixture solution of 2-chloro-5,6-dimethyl-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine(0.5 g, 1.8 mmol) in dimethylformamide(10 ml). The reaction mixture was stirred for 5 hours at 130° C., cooled to a room temperature, diluted with dichloromethane, and then washed with aqueous sodium hydroxide and water. The separated organic layer was dried over anhydrous magnesium sulfate, concentrated under a reduced pressure, and then purified by column chromatography to give free base form of the titled compound. Ethyl ether saturated with hydrochloric acid was added to a mixture solution of the free base form of the titled compound in ethyl ether. The resulting solid was filtered and dried to obtain 490 mg of the titled compound.

Workup

temperaturecooled to a room temperature
washwashed with aqueous sodium hydroxide and water
dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under a reduced pressure
custompurified by column chromatography

Sources & evidence

ORD record: ord-ba2d68a42ce449589a90e10308960f57
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06352993B1

Reaction notes

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