Diisopropylethylamine → 4-(2-Hydroxy-3-(1-(thieno[3,2-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)phenol

HRID 221642Notes

Reaction equation

HRID 221642 reaction equation
CCN(C(C)C)C(C)C.C([Si](C)(C)[O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH:24]2[CH2:26][O:25]2)=[CH:18][CH:17]=1)(C)(C)C.Cl.[N:30]1[C:35]2[CH:36]=[CH:37][S:38][C:34]=2[C:33]([N:39]2[CH2:44][CH2:43][CH:42]([NH2:45])[CH2:41][CH2:40]2)=[N:32][CH:31]=1>CC(O)C.CS(C)=O>[OH:25][CH:24]([CH2:26][NH:45][CH:42]1[CH2:43][CH2:44][N:39]([C:33]2[C:34]3[S:38][CH:37]=[CH:36][C:35]=3[N:30]=[CH:31][N:32]=2)[CH2:40][CH2:41]1)[CH2:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([OH:15])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 19385012Tert-butyldimethyl(4-(oxiran-2-ylmethoxy)phenoxy)silaneHCID 1317297881-(Thieno[3,2-d]pyrimidin-4-yl)piperidin-4-amine hcl-salt

Product 1

HCID 249370164-(2-Hydroxy-3-(1-(thieno[3,2-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)phenolYield 13%

Reagents, catalysts & solvents 1

HCID 87082799iPrOH DMSOSolvent

Procedure

Synthesis followed SP6 (iPrOH:DMSO 1:1, 1.2 eq. DIEA, 120° C., 48 h), using 200 μmol tert-butyldimethyl(4-(oxiran-2-ylmethoxy)phenoxy)silane and 1-(thieno[3,2-d]pyrimidin-4-yl)piperidin-4-amine HCl-salt to give O-silylated intermediate upon purification by prep. HPLC (reversed phase) and prep. TLC (1 mm silica gel, PE/CH2Cl2/MeOH 6:4:1) with 13% yield. Product was obtained by deprotection according to SP7 and purification by prep. HPLC (reversed phase) with 37% 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-be90e808a8f6403d8e22cf63c06a0b38
Source dataset
uspto-grants-2012_06
Patent number
US08207174B2

Reaction notes

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