Phenacyl bromide → HCID 86586569, compound

HRID 1836737Notes

Reaction equation

HRID 1836737 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:10][NH:9][C:8](=[O:11])[NH:7][C:6]=2[N:12]=1.[Br:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16]>C(O)C>[Br-:13].[CH3:1][C:2]1[N+:3]([CH2:14][C:15](=[O:16])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][C:5]2[CH2:10][NH:9][C:8](=[O:11])[NH:7][C:6]=2[N:12]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 2226937-Methyl-3,4-dihydropyrimido(4,5-d)pyrimidin-2(1H)-one

Product 1

HCID 86586569HCID 86586569, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methyl-7-oxo-5,6,7,8-tetrahydropyrimidino[4,5-d]pyrimidine (0.1 g, 0.6 mmole) and 2-bromo-1-phenyl-1-ethanone (0.12 g, 0.6 mmole) in ethanol (20 mL) were heated at reflux for 32 hr. After cooling, the precipitated hydrobromide (mp>310 C.) of the starting heterocycle was filtered out, and the filtrate was diluted with ether to form a precipitate which was recrystalized from methanol-ether to yield 47.5 mg of the title compound, mp 249-250 C.

Workup

  1. temperatureat reflux for 32 hr
  2. temperatureAfter cooling
  3. filtrationthe precipitated hydrobromide (mp>310 C.) of the starting heterocycle was filtered out
  4. additionthe filtrate was diluted with ether
  5. customto form a precipitate which
  6. customwas recrystalized from methanol-ether

Sources & evidence

ORD record
ord-e0e357ba59154d90813a443521245958
Source dataset
uspto-grants-2004_08
Patent number
US06777557B2

Reaction notes

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