Triethylamine → 2-methyl-5-(7-phenyl-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-pyrimidin-4-ylamine

HRID 2294011Notes

Reaction equation

HRID 2294011 reaction equation
Cl[CH2:2][C:3]1[C:4]([NH2:10])=[N:5][C:6]([CH3:9])=[N:7][CH:8]=1.C(N(CC)CC)C.[C:18]1([C:24]2[CH:33]=[C:32]3[C:27]([CH2:28][CH2:29][NH:30][CH2:31]3)=[CH:26][CH:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[CH3:9][C:6]1[N:5]=[C:4]([NH2:10])[C:3]([CH2:2][N:30]2[CH2:29][CH2:28][C:27]3[C:32](=[CH:33][C:24]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:25][CH:26]=3)[CH2:31]2)=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 324007-Phenyl-1,2,3,4-tetrahydroisoquinolineHCID 4212454-Amino-5-(chloromethyl)-2-methylpyrimidine

Product 1

HCID 214736992-methyl-5-(7-phenyl-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-pyrimidin-4-ylamineYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 0.17 g (0.00088 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine in 10 ml of dimethylformamide was treated with 0.30 ml (0.0021 mol) of triethylamine and 0.184 g (0.00088 mol) of 7-phenyl-1,2,3,4-tetrahydro-isoquinoline and the mixture was stirred at room temperature under argon for 18 hours. The solvent was distilled off in a high vacuum. The residue was partitioned between dichloromethane/water, extracted and dried over MgSO4. After removing the solvent the residue was chromatographed over silica gel with ethyl acetate as the eluent. 0.22 g (76%) of 2-methyl-5-(7-phenyl-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-pyrimidin-4-ylamine was obtained as a light yellowish solid; m.p. 147°-149°.

Workup

  1. distillationThe solvent was distilled off in a high vacuum
  2. customThe residue was partitioned between dichloromethane/water
  3. extractionextracted
  4. dry with materialdried over MgSO4
  5. customAfter removing the solvent the residue
  6. customwas chromatographed over silica gel with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-ccd32a52a53c4457a4e475fcb3e7686e
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

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