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

HRID 34446Notes

Reaction equation

HRID 34446 reaction equation
Cl.CN([CH2:5][C:6]1[C:7](=[O:13])[NH:8][C:9](=[O:12])[NH:10][CH:11]=1)C.[NH2:14][C:15]1[C:16]([CH3:25])=[CH:17][CH:18]=[C:19]2[C:24]=1[N:23]=[CH:22][CH:21]=[CH:20]2>C(O)CO>[NH2:14][C:15]1[C:16]([CH3:25])=[CH:17][C:18]([CH2:5][C:6]2[C:7](=[O:13])[NH:8][C:9](=[O:12])[NH:10][CH:11]=2)=[C:19]2[C:24]=1[N:23]=[CH:22][CH:21]=[CH:20]2

Participants

4

Reactant 2

HCID 2315568-Quinolinamine, 7-methyl-HCID 122674355-[(dimethylamino)methyl]-1H-pyrimidine-2,4-dione;hydrochloride

Product 1

HCID 201298195-(8-Amino-7-methyl-5-quinolylmethyl)-2,4(1H,3H)-pyrimidinedioneYield 78%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

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.

Workup

  1. temperatureThe mixture was cooled
  2. customthe precipitated solid was collected
  3. washwashed with ethanol and ether
  4. customdried
  5. customThis crude product was purified by suspension in 550 ml of boiling ethanol
  6. customcollection of the insoluble product
  7. customYield

Sources & evidence

ORD record
ord-511a7405e34546f59e9f01059d84fb40
Source dataset
uspto-grants-1988_08
Patent number
US04761475

Reaction notes

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