Hydrochloric Acid → 7(8H)-Pteridinone

HRID 599270Notes

Reaction equation

HRID 599270 reaction equation
FC1C=C(C)C([C:9]2[C:18](=[O:19])[N:17](C)[C:16]3[N:15]=[C:14](NC)[N:13]=[CH:12][C:11]=3[N:10]=2)=CC=1NC(=O)C.Cl>CO>[N:15]1[C:16]2[NH:17][C:18](=[O:19])[CH:9]=[N:10][C:11]=2[CH:12]=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67063152HCID 67063152, compound

Product 1

HCID 5905497(8H)-PteridinoneYield 160.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(2-fluoro-4-methyl-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropteridin-6-yl)phenyl)acetamide (1.5 g, 4.2 mmol) and conc. HCl (1 mL) in MeOH (20 mL) was heated at reflux overnight. The solvent was removed under reduced pressure. Water was added, and the mixture basified to pH=8. The resulting precipitate was collected by filtration and dried to give 6-(5-amino-4-fluoro-2-methylphenyl)-8-methyl-2-methylamino)pteridin-7(8H)-one (1.0 g, 78% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.70 (s, 0.3 H), 8.62 (s, 0.7 H) □7.96 (m, 0.7 H) □7.85 (m, 0.3 H) □6.88 (d, J=12.4 Hz, 1 H), 6.78 (d, J=9.2 Hz, 1 H), 4.98 (s, 2 H), 3.56 (s, 2 H), 3.48 (s, 1 H) □2.91 (d, J=4 Hz, 3 H), 2.03 (s, 3 H). MS (ESI) m/z: 315.2 [M+H]+.

Workup

  1. temperatureat reflux overnight
  2. customThe solvent was removed under reduced pressure
  3. additionWater was added
  4. filtrationThe resulting precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-8d6fe894c6904a4baa59bcc76a7b616c
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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