1-(5-Phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine → (R)-4-(2-hydroxy-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)phenol

HRID 221637Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 221637
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 690415621-(5-Phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amineHCID 86623598(R)-2-((4-(methoxymethoxy)phenoxy)methyl)oxirane

Produkt 1

HCID 25001235(R)-4-(2-hydroxy-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)phenolAusbeute 57 %

Versuchsvorschrift

Synthesis followed SP6 (4 h), using 250 μmol (R)-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 57% 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 55% 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-49cd62d50f9e4ea5a7e04bd296c2b218
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207174B2

Notizen zur Reaktion

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