(S)-2-((4-(methoxymethoxy)phenoxy)methyl)oxirane → (S)-4-(2-hydroxy-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)phenol

HRID 221638Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 221638
COC[O:4][C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C@@H:11]2[CH2:13][O:12]2)=[CH:7][CH:6]=1.[C:16]1([C:22]2[C:30]3[C:29]([N:31]4[CH2:36][CH2:35][CH:34]([NH2:37])[CH2:33][CH2:32]4)=[N:28][CH:27]=[N:26][C:25]=3[S:24][CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[OH:12][C@@H:11]([CH2:13][NH:37][CH:34]1[CH2:35][CH2:36][N:31]([C:29]2[C:30]3[C:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:23][S:24][C:25]=3[N:26]=[CH:27][N:28]=2)[CH2:32][CH2:33]1)[CH2:10][O:9][C:8]1[CH:7]=[CH:6][C:5]([OH:4])=[CH:15][CH:14]=1

Komponenten

3

Edukt 2

HCID 44126707(S)-2-((4-(methoxymethoxy)phenoxy)methyl)oxiraneHCID 690415621-(5-Phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine

Produkt 1

HCID 24936487(S)-4-(2-hydroxy-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)phenolAusbeute 58 %

Versuchsvorschrift

Synthesis followed SP6 (4 h), using 250 μmol (S)-2-((4-(methoxymethoxy)phenoxy)methyl)oxirane and 1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine to give O-MOM intermediate upon purification by prep. TLC (2 mm silica gel, PE/CH2Cl2/MeOH 4:6:1) with 58% yield. Product was obtained by MOM removal according to SP8 (1.5 eq. TosOH, 10 h) and purification by prep. TLC (1 mm silica gel, CH2Cl2/MeOH 90:10) with 61% yield.

Aufarbeitung

  1. customSynthesis
  2. customSP6 (4 h)
  3. customto give O-MOM intermediate
  4. customupon purification by prep
  5. customProduct was obtained by MOM removal
  6. customaccording to SP8 (1.5 eq. TosOH, 10 h) and purification by prep

Quellen und Nachweise

ORD-Eintrag
ord-8bba54e8361c4dbdad1911b39bd75ac1
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207174B2

Notizen zur Reaktion

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