5,6,7,8-Tetrahydroisoquinoline → 2-(4-Amino-2-methyl-pyrimidin-5-ylmethyl)-5,6,7,8-tetrahydro-isoquinolinium chloride hydrochloride

HRID 2294014Notes

Reaction equation

HRID 2294014 reaction equation
[ClH:1].[Cl:2][CH2:3][C:4]1[C:5]([NH2:11])=[N:6][C:7]([CH3:10])=[N:8][CH:9]=1.[CH:12]1[C:21]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=2[CH:15]=[CH:14][N:13]=1>CN(C)C=O>[ClH:2].[Cl-:1].[NH2:11][C:5]1[C:4]([CH2:3][N+:13]2[CH:14]=[CH:15][C:16]3[CH2:17][CH2:18][CH2:19][CH2:20][C:21]=3[CH:12]=2)=[CH:9][N:8]=[C:7]([CH3:10])[N:6]=1

Participants

4

Reactant 2

HCID 1190105,6,7,8-TetrahydroisoquinolineHCID 214736115-(Chloromethyl)-2-methylpyrimidin-4-amine--hydrogen chloride (1/1)

Product 1

HCID 214736402-(4-Amino-2-methyl-pyrimidin-5-ylmethyl)-5,6,7,8-tetrahydro-isoquinolinium chloride hydrochlorideYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 11.6 g (0.060 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine hydrochloride in 40 ml of dimethyl-formamide was treated with 8.0 ml (0.060 mol) of 5,6,7,8-tetra-hydro-isoquinoline, dissolved at 120° and stirred at 800 for 16 hours. The mixture was cooled, suction filtered, washed with a small amount of dimethylformamide, then with ethyl acetate and dried in a vacuum. 16.5 g (84%) of 2-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5,6,7,8-tetrahydro-isoquinolinium chloride hydrochloride were obtained as yellowish crystals; m.p. 242°-244°.

Workup

  1. dissolutiondissolved at 120°
  2. temperatureThe mixture was cooled
  3. filtrationsuction filtered
  4. washwashed with a small amount of dimethylformamide
  5. dry with materialwith ethyl acetate and dried in a vacuum

Sources & evidence

ORD record
ord-3dfc5734710d4f9f8d7c6e1180668cdf
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

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