Dimethyl Sulfoxide → 5-{9-(Cyclopropylmethyl)-8-[(3S)-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine

HRID 421399

Reaktionsgleichung

Reaktionsgleichung von HRID 421399
CS(C)=O.Cl[C:6]1[N:7]([CH2:28][CH:29]2[CH2:31][CH2:30]2)[C:8]2[C:13]([N:14]=1)=[C:12]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[N:11]=[C:10]([C:21]1[CH:22]=[N:23][C:24]([NH2:27])=[N:25][CH:26]=1)[N:9]=2.[CH3:32][C@H:33]1[CH2:38][NH:37][CH2:36][CH2:35][NH:34]1>C(Cl)Cl.CO>[CH:29]1([CH2:28][N:7]2[C:6]([N:37]3[CH2:36][CH2:35][NH:34][C@@H:33]([CH3:32])[CH2:38]3)=[N:14][C:13]3[C:8]2=[N:9][C:10]([C:21]2[CH:22]=[N:23][C:24]([NH2:27])=[N:25][CH:26]=2)=[N:11][C:12]=3[N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH2:31][CH2:30]1

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 27342192-Methylpiperazine, (S)-2×HCID 593335195-[8-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]pyrimidin-2-amine

Produkt 1

HCID 593335285-{9-(Cyclopropylmethyl)-8-[(3S)-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amineAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226129Dichloromethane methanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A dimethyl sulfoxide suspension (5 ml) of 5-[8-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]pyrimidin-2-amine (476.1 mg, 1.23 mmol) and (2S)-2-methylpiperazine (616.4 mg, 6.15 mmol) was heated at 100° C. to dissolve and the resulting mixture was stirred at 85° C. for 18.5 hours. (2S)-2-Methylpiperazine (123.3 mg, 1.23 mmol) was added and the resulting mixture was further stirred at 85° C. for 5.5 hours, left standing to cool, poured into methylene chloride-methanol (10:1), and washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous sodium sulfate, the mixture was filtrated, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by medium pressure silica gel column chromatography (methylene chloride:methanol=32:1 to 9:1) to give the title compound (516.0 mg, 93%) as a pale yellow solid.

Aufarbeitung

  1. dissolutionto dissolve
  2. stirringthe resulting mixture was further stirred at 85° C. for 5.5 hours
  3. waitleft
  4. temperatureto cool
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationthe mixture was filtrated
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customthe resulting residue was purified by medium pressure silica gel column chromatography (methylene chloride:methanol=32:1 to 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-28aa3808aaae4469862e75b960b0740b
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097622B2

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