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

HRID 275907
Notes
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Reaction equation

HRID 275907 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7852PropylamineHCID 8471TriethylamineHCID 183157432-Chloro-5,6-dimethyl-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine

Product 1

HCID 183157355,6-Dimethyl-2-(propylamino)-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine hydrochloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 6344
Dichloromethane
Solvent

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

  1. temperaturecooled to a room temperature
  2. washwashed with aqueous sodium hydroxide and water
  3. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes