Water → 7-[(3aS,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethylhexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 1054527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1054527
[N:1]([CH2:4][C@@H:5]1[C@H:9]2[O:10][C:11]([CH3:14])([CH3:13])[O:12][C@H:8]2[C@H:7]([N:15]2[C:19]3[N:20]=[CH:21][N:22]=[C:23]([N:24]=[N+]=[N-])[C:18]=3[CH:17]=[CH:16]2)[CH2:6]1)=[N+]=[N-].CP(C)C.O>C1COCC1>[NH2:1][CH2:4][C@@H:5]1[C@H:9]2[O:10][C:11]([CH3:14])([CH3:13])[O:12][C@H:8]2[C@H:7]([N:15]2[C:19]3[N:20]=[CH:21][N:22]=[C:23]([NH2:24])[C:18]=3[CH:17]=[CH:16]2)[CH2:6]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 68983TrimethylphosphineHCID 867057467-[(3aS,4R,6R,6aR)-6-(Azidomethyl)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-4-azido-7H-pyrrolo[2,3-d]pyrimidine

Produkt 1

HCID 678180027-[(3aS,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethylhexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amineAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

7-[(3aS,4R,6R,6aR)-6-(Azidomethyl)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-4-azido-7H-pyrrolo[2,3-d]pyrimidine (3.933 g, 11.1 mmol) was dissolved in THF (20 ml) and trimethylphosphane (1M in THF) (44.3 ml, 44.3 mmol) was added at r.t. under N2 and the reaction stirred overnight. Water (4 ml) was added and the reaction was left for 15 mins. The solvents were removed in vacuo to give the crude product. The product was purified by silica flash column chromatography using between 100% DCM to 20% 2M NH3 in MeOH:80% DCM as eluent to give the product as pale yellow foam (2.706 g, 81%): MS (ESI+) for C15H21N5O2 m/z 304.2 [M+H]+, 326.1 [M+Na]+; LCMS: Compound in solvent front; 1H NMR (500 MHz, CDCl3) δ 8.10 (s, 1H), 7.27 (d, J=3.63 Hz, 1H), 6.63 (d, J=3.63 Hz, 1H), 5.02 (dt, J=12.14, 6.23 Hz, 1H), 4.92-4.99 (m, 1H), 4.48-4.61 (m, 1H), 2.82-2.91 (m, 1H), 2.71-2.82 (m, 1H), 2.40 (dt, J=12.65, 6.52 Hz, 1H), 2.27 (m, 1H), 2.04 (q, J=12.14 Hz, 1H), 1.56 (s, 3H), 1.31 (s, 3H).

Aufarbeitung

  1. waitthe reaction was left for 15 mins
  2. customThe solvents were removed in vacuo
  3. customto give the crude product
  4. customThe product was purified by silica flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8e850b2b2956450e85e2ce34302779b9
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394310B2

Notizen zur Reaktion

Wird geladen…