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

HRID 2256096Notes

Reaction equation

HRID 2256096 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 N2 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 (2E, 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-fa7db4b60af1494094b30e144285cc80
Source dataset
uspto-grants-1997_08
Patent number
US05654307

Reaction notes

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