Reaction #62724

Reaction equation

5-[(dimethylamino)methyl]uracil hydrochloride

8-amino-7-methylquinoline

→

title compound

Yield 78.0%

5-(8-Amino-7-methyl-5-quinolylmethyl)-2,4(1H,3H)-pyrimidinedione

Yield 78.0%

Solvents

ethylene glycol

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled
2. 2
   Otherthe precipitated solid was collected
3. 3
   Washwashed with ethanol and ether
4. 4
   Otherdried
5. 5
   OtherThis crude product was purified by suspension in 550 ml of boiling ethanol
6. 6
   Othercollection of the insoluble product
7. 7
   OtherYield

Procedure

A mixture of 8.36 g (0.0406 mole) of 5-[(dimethylamino)methyl]uracil hydrochloride (B. Roth, J. Z. Strelitz, and B. S. Rauckman, J. Med. Chem. 23, 379 (1980) and 6.43 g (0.0406 mole) of 8-amino-7-methylquinoline (R. Long and K. Schofield, J. Chem. Soc. 1953, 2350) in 60 ml of ethylene glycol under nitrogen was heated at 135° for 4 hours. The mixture was cooled and the precipitated solid was collected, washed with ethanol and ether and dried. This crude product was purified by suspension in 550 ml of boiling ethanol and collection of the insoluble product. Yield, 8.90 g of the title compound (78%) m.p. 302°-305° (dec.). Anal. Calcd for C21H20N4 : C, 76.89; H, 6.14; N, 17.06. Found: C, 76.82; H, 6.17; N, 17.04.

Source