Triethylamine → 2-methyl-5-(6-phenyl-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-pyrimidin-4-ylamine

HRID 2294008Notes

Reaction equation

HRID 2294008 reaction equation
Cl.Cl[CH2:3][C:4]1[C:5]([NH2:11])=[N:6][C:7]([CH3:10])=[N:8][CH:9]=1.C(N(CC)CC)C.[C:19]1([C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[CH2:31][NH:30][CH2:29][CH2:28]3)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[CH3:10][C:7]1[N:6]=[C:5]([NH2:11])[C:4]([CH2:3][N:30]2[CH2:29][CH2:28][C:27]3[C:32](=[CH:33][CH:34]=[C:25]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:26]=3)[CH2:31]2)=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 323966-Phenyl-1,2,3,4-tetrahydroisoquinolineHCID 214736115-(Chloromethyl)-2-methylpyrimidin-4-amine--hydrogen chloride (1/1)

Product 1

HCID 98623392-methyl-5-(6-phenyl-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-pyrimidin-4-ylamineYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 0.20 g (0.00080 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine hydrochloride in 10 ml of dimethylformamide was treated with 0.34 ml (0.0024 mol) of triethylamine and 0.19 g (0.00097 mol) of 6-phenyl-1,2,3,4-tetrahydro-isoquinoline and the mixture was stirred at room temperature under argon for 60 hours The mixture was completely freed from the solvents. The residue was partitioned between dichloromethane and water, extracted, chromatographed over silica gel with acetonitrile/methanol 5:1 as the eluent and digested in diethyl ether. 0.16 g (61%) of 2-methyl-5-(6-phenyl-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-pyrimidin-4-ylamine was obtained as white crystals; m.p. 186°-188°. A further 0.03 g of pale yellow crystals was recovered from the mother liquor.

Workup

  1. customThe residue was partitioned between dichloromethane and water
  2. extractionextracted
  3. customchromatographed over silica gel with acetonitrile/methanol 5:1 as the eluent and digested in diethyl ether

Sources & evidence

ORD record
ord-5c6ec1e12bb3414890f5efa3f07dd982
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

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