Potassium Carbonate → 6-(3-Chloro-4-methoxyphenyl)pyrido[3,2-d]pyrimidine-2,4-diamine

HRID 1517412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517412
[NH2:1][C:2]1[N:3]=[C:4]([NH2:13])[C:5]2[N:11]=[C:10](Cl)[CH:9]=[CH:8][C:6]=2[N:7]=1.C([O-])([O-])=O.[K+].[K+].[Cl:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[N:3]=[C:4]([NH2:13])[C:5]2[N:11]=[C:10]([C:23]3[CH:24]=[CH:25][C:26]([O:27][CH3:28])=[C:21]([Cl:20])[CH:22]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 32475223-Chloro-4-methoxybenzeneboronic acidHCID 133817146-Chloropyrido[3,2-d]pyrimidine-2,4-diamine

Produkt 1

HCID 251545636-(3-Chloro-4-methoxyphenyl)pyrido[3,2-d]pyrimidine-2,4-diamineAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A suspension of 2,4-diamino-6-chloropyrido[3,2-d]pyrimidine (464 mg, 2.37 mmole), K2CO3 (1332 mg, 9.64 mmole), 3-chloro-4-methoxyphenyl boronic acid (907 mg, 4.86 mmole) in 1,4-dioxane (35.5 ml) and water (7 ml) was purged with a stream of nitrogen for 15 minutes. Then, tetrakis(triphenylphosphine)palladium(0) (278 mg, 0.24 mmole) was added and the reaction mixture was heated at reflux under a N2 atmosphere for 4 hours. Upon cooling, the mixture was partitioned between CH2Cl2 and a saturated aqueous sodium bicarbonate solution. The organic phase was dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified by silica gel flash chromatography, using methanol and 1% Et3N in CH2Cl2 as eluent, gradually increasing the methanol concentrations from 5% to 10%, to afford the pure title compound (277 mg, yield 39%) which was characterized by its mass spectrum as follows: MS (m/z): 302 ([M+H]+, 100).

Aufarbeitung

  1. customwas purged with a stream of nitrogen for 15 minutes
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux under a N2 atmosphere for 4 hours
  4. temperatureUpon cooling
  5. customthe mixture was partitioned between CH2Cl2
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe crude residue was purified by silica gel flash chromatography
  10. temperaturegradually increasing
  11. concentrationthe methanol concentrations from 5% to 10%

Quellen und Nachweise

ORD-Eintrag
ord-fdeb8fc369fa4ad5986009274d9f62eb
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232278B2

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