Potassium Carbonate → (+/-)-2-(2-Amino-5-phenylmethylthio-thiazolo[4,5-d]pyrimidin-7-ylamino)-hexan-1-ol

HRID 1831462

Reaktionsgleichung

Reaktionsgleichung von HRID 1831462
[C:1]1([CH2:7][S:8][C:9]2[N:10]=[C:11](Cl)[C:12]3[S:17][C:16]([NH2:18])=[N:15][C:13]=3[N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][CH2:21][CH2:22][CH2:23][CH:24]([NH2:27])[CH2:25][OH:26].C(=O)([O-])[O-].[K+].[K+]>>[NH2:18][C:16]1[S:17][C:12]2[C:11]([NH:27][CH:24]([CH2:23][CH2:22][CH2:21][CH3:20])[CH2:25][OH:26])=[N:10][C:9]([S:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:14][C:13]=2[N:15]=1

Komponenten

4

Edukt 3

HCID 11430Potassium CarbonateHCID 249006DL-2-Amino-1-hexanolHCID 112782745-(Benzylthio)-7-chloro[1,3]thiazolo[4,5-d]pyrimidin-2-amine

Produkt 1

HCID 10200369(+/-)-2-(2-Amino-5-phenylmethylthio-thiazolo[4,5-d]pyrimidin-7-ylamino)-hexan-1-olAusbeute 17,6 %

Versuchsvorschrift

5-Phenylmethylthio-7-chloro-thiazolo[4,5-d]pyrimidin-2-ylamin (100 mg, 0.32 mmol), DL-2-amino-1-hexanol (295 μL, 2.3 mmol) and potassium carbonate (124 mg, 0.90 mmol) were heated for 24 hours as in Example 1. The solution was filtered and the solvent was evaporated. The crude product was flash chromatographed on silica (gradient eluent—ammonia:ethylacetate:dichloromethane, 1:69:30 to 1:99:0) resulting in 22 mg (17% yield) of the title compound as a yellow solid.

Aufarbeitung

  1. filtrationThe solution was filtered
  2. customthe solvent was evaporated
  3. customchromatographed on silica (gradient eluent—ammonia:ethylacetate:dichloromethane, 1:69:30 to 1:99:0)

Quellen und Nachweise

ORD-Eintrag
ord-0a1aca006ea24e61ae7b7c3a54cd4258
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07067657B2

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