Diisopropylethylamine → 5,6,7,8-tetrahydro-N-(4-(trifluoromethylsulfonyl)phenyl)pyrido[4,3-d]pyrimidin-4-amine

HRID 19633

Reaktionsgleichung

Reaktionsgleichung von HRID 19633
C([N:8]1[CH2:31][CH2:30][C:11]2[N:12]=[CH:13][N:14]=[C:15]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])=[CH:19][CH:18]=3)[C:10]=2[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)=O)C.C(N(CC)C(C)C)(C)C>C(Cl)(Cl)Cl>[F:29][C:26]([F:27])([F:28])[S:23]([C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:15]2[C:10]3[CH2:9][NH:8][CH2:31][CH2:30][C:11]=3[N:12]=[CH:13][N:14]=2)=[CH:18][CH:19]=1)(=[O:24])=[O:25]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 593465576-Benzyl-5,6,7,8-tetrahydro-N-(4-(trifluoromethylsulfonyl)phenyl)pyrido[4,3-d]pyrimidin-4-amine

Produkt 1

HCID 593464545,6,7,8-tetrahydro-N-(4-(trifluoromethylsulfonyl)phenyl)pyrido[4,3-d]pyrimidin-4-amineAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

6-Benzyl-5,6,7,8-tetrahydro-N-(4-(trifluoromethylsulfonyl)phenyl)pyrido[4,3-d]pyrimidin-4-amine (270 mg, 0.55 mmol) was dissolved in anhydrous chloroform (10 mL) and 1-chloroethylchloroformate was added (0.18 mL, 1.65 mmol). After stirring for 30 min, N,N-diisopropylethylamine was added (0.24 mL, 1.65 mmol) and the mixture was stirred for an additional 2 h. The chloroform was removed under vacuum and 30 ml of methanol was added and the mixture was heated for 30 min. Upon reaction completion, the methanol was removed and the residue was dissolved in ethyl acetate and washed with sat. NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give the product (163 mg, 83%).

Aufarbeitung

  1. stirringthe mixture was stirred for an additional 2 h
  2. customThe chloroform was removed under vacuum and 30 ml of methanol
  3. additionwas added
  4. temperaturethe mixture was heated for 30 min
  5. customUpon reaction completion
  6. customthe methanol was removed
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. washwashed with sat. NaHCO3 and brine
  9. dry with materialThe organic layer was dried over Na2SO4
  10. filtrationfiltered
  11. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-4801c6f6649e49269c71b088f756b648
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745451B2

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