Hydrochloric Acid → {2-[3-(7-Methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-ureido]-ethyl}-carbamic acid tert-butyl ester

HRID 550829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 550829
[CH3:1][O:2][C:3]1[C:4]2[N:11]=[C:10]([NH2:12])[S:9][C:5]=2[N:6]=[CH:7][N:8]=1.N1C=CC=CC=1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[C:31]([O:35][C:36]([NH:38][CH2:39][CH2:40][NH:41][C:42](=O)[OH:43])=[O:37])([CH3:34])([CH3:33])[CH3:32].Cl>O1CCCC1>[C:31]([O:35][C:36](=[O:37])[NH:38][CH2:39][CH2:40][NH:41][C:42]([NH:12][C:10]1[S:9][C:5]2[N:6]=[CH:7][N:8]=[C:3]([O:2][CH3:1])[C:4]=2[N:11]=1)=[O:43])([CH3:34])([CH3:32])[CH3:33]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 94429TriphosgeneHCID 22242930(2-((Tert-butoxycarbonyl)amino)ethyl)carbamic acidHCID 574765977-Methoxy-[1,3]thiazolo[5,4-d]pyrimidin-2-amine

Produkt 1

HCID 59011968{2-[3-(7-Methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-ureido]-ethyl}-carbamic acid tert-butyl esterAusbeute 36,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of 7-methoxy-thiazolo[5,4-d]pyrimidin-2-ylamine (233 mg, 1.28 mmol) and pyridine (310 μL, 3.53 mmol) in tetrahydrofuran (6 mL) at 25° C. was treated with a solution of triphosgene (190 mg, 0.64 mmol) in tetrahydrofuran (2 mL) followed by (2-tert-butoxycarbonylamino-ethyl)-carbamic acid (225 mg, 1.40 mmol). The reaction was stirred at 25° C. overnight. At this time, the reaction was treated with a 1N aqueous hydrochloric acid solution and was stirred at 25° C. for an additional 30 min. At this time, the resulting precipitate was collected by filtration and was washed with a 1N aqueous hydrochloric acid solution and diethyl ether to afford {2-[3-(7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-ureido]-ethyl}-carbamic acid tert-butyl ester (170 mg, 36.8%) as a pink solid; LRMS for C14H20N6O4S (M+H)+ at m/z=369.

Aufarbeitung

  1. stirringwas stirred at 25° C. for an additional 30 min
  2. filtrationAt this time, the resulting precipitate was collected by filtration
  3. washwas washed with a 1N aqueous hydrochloric acid solution and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-af9c45efb9cd4adea7f552429aaa6335
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947692B2

Notizen zur Reaktion

Wird geladen…