Oxalyl chloride → 6-Bromopyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 1362102Notes

Reaction equation

HRID 1362102 reaction equation
C(Cl)(=O)[C:2](Cl)=[O:3].[NH2:7][C:8]1[N:16]=[CH:15][C:14]([Br:17])=[CH:13][C:9]=1[C:10]([NH2:12])=[O:11]>C1(C)C=CC=CC=1>[Br:17][C:14]1[CH:15]=[N:16][C:8]2[NH:7][C:2](=[O:3])[NH:12][C:10](=[O:11])[C:9]=2[CH:13]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 529879382-Amino-5-bromopyridine-3-carboxamide

Product 1

HCID 235841046-Bromopyrido[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 154.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Oxalyl chloride (100 mL, 1.16 mmol) was added dropwise to a suspension of 2-amino-5-bromo-nicotinamide (500 mg, 2.31 mmol) in toluene (5 mL) and the resulting mixture was heated to reflux for 4 h. The reaction mixture was cooled and the mustard-colored solid which had formed was collected by filtration. The solid was washed with a small amount of water, MeOH, and then dried under high vacuum (40° C.) overnight to give the title compound (435 mg, 77%): 1H NMR (300 MHz, DMSO-d6) δ 11.86 (s, 1H), 11.60 (s, 1H), 8.72 (d, J=2.5 Hz, 1H), 8.35 (d, J=2.5 Hz, 1H); 13C NMR (126 MHz, DMSO-d6) δ 161.4, 154.8, 151.2, 150.17, 137.8, 112.6, 111.6.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 4 h
  3. temperatureThe reaction mixture was cooled
  4. customthe mustard-colored solid which had formed
  5. filtrationwas collected by filtration
  6. washThe solid was washed with a small amount of water, MeOH
  7. customdried under high vacuum (40° C.) overnight

Sources & evidence

ORD record
ord-b56a99e3721c402f904e63de4fa7172d
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

Loading…