Tert-butyldimethyl(4-(oxiran-2-ylmethoxy)phenoxy)silane → 4-(2-Hydroxy-3-(1-(5-(thiophen-2-yl)thieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)phenol

HRID 221644Notes

Reaction equation

HRID 221644 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH:15]2[CH2:17][O:16]2)=[CH:9][CH:8]=1)(C)(C)C.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25]1[C:33]2[C:32]([N:34]3[CH2:39][CH2:38][CH:37]([NH2:40])[CH2:36][CH2:35]3)=[N:31][CH:30]=[N:29][C:28]=2[S:27][CH:26]=1>>[OH:16][CH:15]([CH2:17][NH:40][CH:37]1[CH2:36][CH2:35][N:34]([C:32]2[C:33]3[C:25]([C:21]4[S:20][CH:24]=[CH:23][CH:22]=4)=[CH:26][S:27][C:28]=3[N:29]=[CH:30][N:31]=2)[CH2:39][CH2:38]1)[CH2:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([OH:6])=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 19385012Tert-butyldimethyl(4-(oxiran-2-ylmethoxy)phenoxy)silaneHCID 690398001-(5-(2-Thienyl)thieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine

Product 1

HCID 249364924-(2-Hydroxy-3-(1-(5-(thiophen-2-yl)thieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)phenolYield 27%

Procedure

Synthesis followed SP6 (5 h), using 150 μmol tert-butyldimethyl(4-(oxiran-2-ylmethoxy)phenoxy)silane and 1-(5-(2-thienyl)thieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine to give O-silylated intermediate upon purification by prep. HPLC (reversed phase) and prep. TLC (1 mm silica gel, CH2Cl2MeOH 95:5) with 27% yield. Product was obtained by deprotection according to SP7 and purification by prep. HPLC (reversed phase) with 27% yield.

Workup

  1. customSynthesis
  2. customSP6 (5 h)
  3. customto give O-silylated intermediate
  4. customupon purification by prep
  5. customProduct was obtained by deprotection
  6. customaccording to SP7 and purification by prep

Sources & evidence

ORD record
ord-2c31f8bb0fd148ef82fd4ffc206057a9
Source dataset
uspto-grants-2012_06
Patent number
US08207174B2

Reaction notes

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