p-Toluenesulfonic acid → HCID 11682137, compound

HRID 1517398Notes

Reaction equation

HRID 1517398 reaction equation
Cl.[NH2:2][C:3]1[NH:4][C:5](=O)[C:6]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=3)[CH:10]=[CH:9][C:7]=2[N:8]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.S([O-])([O-])(=O)=O.[NH4+].[NH4+].[NH:42]1[CH2:47][CH2:46][O:45][CH2:44][CH2:43]1>C1(C)C=CC=CC=1>[NH2:2][C:3]1[N:4]=[C:5]([N:42]2[CH2:47][CH2:46][O:45][CH2:44][CH2:43]2)[C:6]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=3)[CH:10]=[CH:9][C:7]=2[N:8]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8083MorpholineHCID 6097028Ammonium SulfateHCID 136389260HCID 136389260, compound

Product 1

HCID 11682137HCID 11682137, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-amino-6-(3,4-dimethoxyphenyl)pyrido[3,2-d]pyrimidin-4(3H)-one hydrochloride (332 mg; 1 mmole) was suspended in toluene (10 ml) with a catalytic amount of p-toluenesulfonic acid and ammonium sulfate. Then, 1,1,1,3,3,3-hexamethyldisilizane (3.2 ml; 15 mmole) and morpholine (0.53 ml; 6 mmole) were added. The mixture was refluxed for 24 hours and evaporated to dryness. The residue was purified by silica gel column chromatography, using a mixture of CH2Cl2/MeOH: 96:4 as eluent, resulting in the pure title compound (120 mg; yield 32%) which was characterized by its mass spectrum as follows: MS (m/z): 368 ([M+H]+, 100).

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. customevaporated to dryness
  3. customThe residue was purified by silica gel column chromatography
  4. additiona mixture of CH2Cl2/MeOH

Sources & evidence

ORD record
ord-c7942ebb85ae44ddb06c00d5a416ab99
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

Loading…