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Acetone → (S)-4-(2-chloro-6-isopropyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine

HRID 1626652
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1626652
Cl.[Cl:2][C:3]1[N:4]=[C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[C:6]2[CH2:11][NH:10][CH2:9][C:7]=2[N:8]=1.C(O)(C(F)(F)F)=O.[CH3:26][C:27]([CH3:29])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.C(O)(=O)C>[Cl:2][C:3]1[N:4]=[C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[C:6]2[CH2:11][N:10]([CH:27]([CH3:29])[CH3:26])[CH2:9][C:7]=2[N:8]=1
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Komponenten

7

Edukt 4

HCID 180AcetoneHCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 86663150(S)-4-(2-chloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine hydrochloride2×

Produkt 1

HCID 86663166(S)-4-(2-chloro-6-isopropyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 176Acetic AcidKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of (S)-4-(2-chloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine (intermediate 6) as a TFA salt (820 mg, 2.0 mmol) in anhydrous THF (5 ml) was added anhydrous acetone (500 μl) and glacial acetic acid (four drops). The reaction was stirred at RT for 30 minutes after which time sodium triacetoxyborohydride (848 mg, 4.0 mmols) was added. After stirring for a further 30 minutes at RT, the reaction was partitioned between water and DCM. The aqueous phase was extracted into DCM and the organic extracts were combined, dried over magnesium sulphate and concentrated in vacuo to afford the title compound as a brown oil, which was used without further purification.

Aufarbeitung

  1. additionwas added
  2. customthe reaction was partitioned between water and DCM
  3. extractionThe aqueous phase was extracted into DCM
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-987b356a77224a29ac37c05859167b5f
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08785457B2

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