Triethylamine hydrochloride → HCID 57498061, compound
Reaction equation
[C:1]1([NH:7][C:8]2[C:9](=O)[NH:10][C:11](=O)[NH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:16].C(N(CC)CC)C.P(Cl)(Cl)([Cl:26])=O>>[Cl:16][C:11]1[N:10]=[C:9]([Cl:26])[C:8]([NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:13][N:12]=1Participants
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 5-phenylamino-1H-pyrimidine-2,4-dione (0.25 g, 1.23 mmol) in phosphorous oxychloride (5 mL) was heated at 80° C. for 4 h, and room temperature for 20 h. Triethylamine hydrochloride (0.50 g, 3.69 mmol) was added and the reaction was stirred 6d at 80° C. and 6d at room temperature. Phosphorous oxychloride was evaporated (azeotroping with toluene), then the residue was cooled to 0° C. and diluted with ethyl acetate. Excess reagent was carefully quenched with ice-chips, then the mixture was washed with sodium bicarbonate and brine, was dried (sodium sulfate) and was evaporated. Purification by flash chromatography (SiO2) eluted with 1:9 ethyl acetate:hexanes provided (2,4-dichloro-pyrimidin-5-yl)-phenyl-amine (0.20 g, 67% yield) as a yellow oil. 1H-NMR (500 MHz, CDCl3) □ 8.33(s, 1H), 7.36 (t, 2H), 7.12 (m, 3H), 5.93 (s, 1H) ppm; MS (FIA) 335.9/337.9 (M+H); HPLC (method A) 3.554 min.
Workup
- customat room temperature
- customPhosphorous oxychloride was evaporated
- custom(azeotroping with toluene)
- temperaturethe residue was cooled to 0° C.
- additiondiluted with ethyl acetate
- customExcess reagent was carefully quenched with ice-chips
- washthe mixture was washed with sodium bicarbonate and brine
- dry with materialwas dried (sodium sulfate)
- customwas evaporated
- customPurification by flash chromatography (SiO2)
- washeluted with 1:9 ethyl acetate
Sources & evidence
- ORD record
- ord-58dec952bdd844d8ae9b10804fdb4e4e
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07262200B2
Reaction notes
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