Aniline → 4-Anilinopyrido[3,2-d]pyrimidine mesylate

HRID 2287664Notes

Reaction equation

HRID 2287664 reaction equation
Cl[C:2]1[C:3]2[N:11]=[CH:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.[CH3:26][S:27]([OH:30])(=[O:29])=[O:28]>CCO>[S:27]([OH:30])(=[O:29])(=[O:28])[CH3:26].[NH:12]([C:2]1[C:3]2[N:11]=[CH:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 131016394-Chloropyrido(3,2-d)pyrimidine

Product 1

HCID 227368124-Anilinopyrido[3,2-d]pyrimidine mesylateYield 57.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-chloropyrido[3,2-d]pyrimidine (84 mg, 0.5 mmol), aniline (56 mg, 0.6 mmol) and triethylamine (62 mg, 0.6 mmol) in EtOH (2 mL) are refluxed under N with stirring for 2 h. The crude reaction mixture is purified on a preparative tlc plate (silica), eluting once with 3% MeOH in CHCl3. The major band is extracted, and evaporated to dryness under reduced pressure, and the residual solid is dissolved in acetone, (5 mL), filtered, and methanesulfonic acid (32 μL, 0.5 mmol) is added slowly with swirling. The precipitate is collected by suction filtration, rinsed with acetone and dried in a vacuum oven to give 4-anilinopyrido[3,2-d]pyrimidine mesylate (91 mg, 57%) as dull yellow needles. 1H NMR (DMSO) δ 11.75 (1H, slbrs), 9.11 (1H, dd, J=1.5, 4.3 Hz), 8.97 (1H, s), 8.32 (1H, dd, J=1.5, 8.4 Hz), 8.12 (1H, dd, J=4.3, 8.5 Hz), 7.88 (2H, d, J=8.2 Hz), 7.49 (2H, t, J=8.0 Hz), 7.32 (1H, t, J=7.0 Hz), 2.34 (3H, s).

Workup

  1. customThe crude reaction mixture
  2. customis purified on a preparative tlc plate (silica)
  3. washeluting once with 3% MeOH in CHCl3
  4. extractionThe major band is extracted
  5. customevaporated to dryness under reduced pressure
  6. dissolutionthe residual solid is dissolved in acetone, (5 mL)
  7. filtrationfiltered
  8. filtrationThe precipitate is collected by suction filtration
  9. washrinsed with acetone
  10. customdried in a vacuum oven

Sources & evidence

ORD record
ord-7cd95bae60f44e1cb400f6f5f39e8a15
Source dataset
uspto-grants-2000_07
Patent number
US06084095

Reaction notes

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