Acetic Anhydride → 6-bromo-3-methyl-4(3H)-Pteridinone

HRID 1959338Notes

Reaction equation

HRID 1959338 reaction equation
[CH:1](OCC)(OCC)OCC.C(OC(=O)C)(=O)C.[NH2:18][C:19]1[C:20]([C:26]([NH:28][CH3:29])=[O:27])=[N:21][C:22]([Br:25])=[CH:23][N:24]=1>>[Br:25][C:22]1[N:21]=[C:20]2[C:19](=[N:24][CH:23]=1)[N:18]=[CH:29][N:28]([CH3:1])[C:26]2=[O:27]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 151481213-Amino-6-bromo-N-methylpyrazine-2-carboxamide

Product 1

HCID 151481226-bromo-3-methyl-4(3H)-PteridinoneYield 79%

Procedure

A mixture of triethyl orthoformate (32.23 g, 36.17 mL, 217.5 mmol) and acetic anhydride (38.49 g, 35.57 mL, 377.0 mmol) was treated with 3-amino-6-bromo-N-methyl-pyrazine-2-carboxamide (6.7 g, 29.00 mmol) and the resulting solution was heated at reflux for 2 hours. After cooling to RT, the resultant precipitate was collected, washed with EtOAc and dried to give the product as a beige solid (5.52 g, 79% Yield). 1H NMR (400.0 MHz, DMSO) d 3.54 (s, 3H), 8.72 (s, 1H); 9.17 (s, 1H) ppm; MS (ES+) 242.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux for 2 hours
  3. customthe resultant precipitate was collected
  4. washwashed with EtOAc
  5. customdried

Sources & evidence

ORD record
ord-a0d3fa67635e4934a39c604cd30e9977
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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