p-Toluenesulfonic acid → HCID 10313396, compound

HRID 896792

Reaction equation

[C:1]1(C)C=CC(S(O)(=O)=O)=C[CH:2]=1.[NH2:12][C:13]1[C:18]([NH2:19])=[C:17]([CH3:20])[N:16]=[C:15]([Cl:21])[N:14]=1>C(Cl)(Cl)Cl>[Cl:21][C:15]1[N:14]=[C:13]2[C:18]([NH:19][C:1]([CH3:2])=[N:12]2)=[C:17]([CH3:20])[N:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

After adding 10.1 ml of ortho-triethyl acetate, 0.23 g of para-toluenesulfonic acid and 73 ml of 2-methylpyrrolidone to 7.6 g of 4,5-diamino-2-chloro-6-methylpyrimidine, the mixture was heated at 100° C. and then heated and stirred while removing out of the system the ethanol produced during the reaction. After disappearance of the 4,5-diamino-2-chloro-6-methylpyrimidine, the reaction solution was further heated and stirred at 180° C. for 2 hours. After cooling to room temperature, chloroform was added thereto for dilution. The mixture solution was washed with water and then washed with saturated brine, after which the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=95.5) to obtain 1.55 g of the title compound.

Workup

temperatureheated
customwhile removing out of the system the ethanol
customproduced during the reaction
stirringstirred at 180° C. for 2 hours
temperatureAfter cooling to room temperature
washThe mixture solution was washed with water
washwashed with saturated brine
dry with materialafter which the organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (chloroform:methanol=95.5)

Sources & evidence

ORD record: ord-6cfa62c9cb6b4b1088f9bed1d4391718
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919455B2

Linked notes

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