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

HRID 221645Notes

Reaction equation

HRID 221645 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.[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[C:35]3[C:34]([N:36]4[CH2:41][CH2:40][CH:39]([NH2:42])[CH2:38][CH2:37]4)=[N:33][CH:32]=[N:31][C:30]=3[S:29][CH:28]=2)=[CH:23][CH:22]=1>CC(O)C.CS(C)=O>[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[C:35]3[C:34]([N:36]4[CH2:41][CH2:40][CH:39]([NH:42][CH2:17][CH:15]([OH:16])[CH2:14][O:13][C:10]5[CH:9]=[CH:8][C:7]([OH:6])=[CH:12][CH:11]=5)[CH2:38][CH2:37]4)=[N:33][CH:32]=[N:31][C:30]=3[S:29][CH:28]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 19385012Tert-butyldimethyl(4-(oxiran-2-ylmethoxy)phenoxy)silaneHCID 690409951-(5-(4-Fluorophenyl)thieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine

Product 1

HCID 249364914-(3-(1-(5-(4-Fluorophenyl)thieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)-2-hydroxypropoxy)phenolYield 45%

Reagents, catalysts & solvents 1

HCID 87082799iPrOH DMSOSolvent

Procedure

Synthesis followed SP6 (iPrOH:DMSO 1:1, 10 h), using 200 μmol tert-butyldimethyl(4-(oxiran-2-ylmethoxy)phenoxy)silane and 1-(5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine to give O-silylated intermediate upon purification by prep. HPLC (reversed phase) with 45% yield. Product was obtained by deprotection according to SP7 and purification by prep. HPLC (reversed phase) with 74% yield.

Workup

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

Sources & evidence

ORD record
ord-928f906070374f1fb48b21888822a012
Source dataset
uspto-grants-2012_06
Patent number
US08207174B2

Reaction notes

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