Trifluoroacetic acid → 2-Pyrrolidin-1-yl-4-p-tolyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine

HRID 72802Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 72802
C(OC([N:8]1[CH2:29][CH2:28][C:11]2[N:12]=[C:13]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[N:14]=[C:15]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[C:10]=2[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:23]1([C:13]2[N:14]=[C:15]([C:16]3[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=3)[C:10]3[CH2:9][NH:8][CH2:29][CH2:28][C:11]=3[N:12]=2)[CH2:24][CH2:25][CH2:26][CH2:27]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 673698102-Pyrrolidin-1-yl-4-p-tolyl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl ester

Produkt 1

HCID 462019712-Pyrrolidin-1-yl-4-p-tolyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidineAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-Pyrrolidin-1-yl-4-p-tolyl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl ester (0.075 g, 0.19 mmol) in CH2Cl2 (3 mL) was added TFA (3 mL). After 16 h, the mixture was concentrated, diluted with saturated (satd.) aqueous (aq.) NaHCO3, and extracted with CH2Cl2. The combined organic layers were dried and concentrated. Purification by FCC (2 M NH3 in MeOH/CH2Cl2) provided the title compound (0.044 g, 79%). HPLC: Rt=7.7 min. MS (ESI): mass calcd. for C18H22N4, 294.4; m/z found, 295.4 [M+H]+. 1H NMR (CDCl3): 7.42-7.34 (m, 2H), 7.28-7.22 (m, 2H), 3.87 (s, 2H), 3.61-3.58 (m, 4H), 3.20 (t, J=6.2, 2H), 2.82 (t, J=6.2, 2H), 2.39 (s, 3H), 1.97-1.94 (m, 4H).

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. additiondiluted with saturated (satd.) aqueous (aq.) NaHCO3
  3. extractionextracted with CH2Cl2
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customPurification by FCC (2 M NH3 in MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-f20de7c524cd4f7cad3b124e407bd409
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829011B2

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