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

HRID 221640Notes

Reaction equation

HRID 221640 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.[CH3:30][C:31]1[N:32]=[C:33]([N:40]2[CH2:45][CH2:44][CH:43]([NH2:46])[CH2:42][CH2:41]2)[C:34]2[CH:39]=[CH:38][S:37][C:35]=2[N:36]=1>CC(O)C.CS(C)=O>[OH:25][CH:24]([CH2:26][NH:46][CH:43]1[CH2:42][CH2:41][N:40]([C:33]2[C:34]3[CH:39]=[CH:38][S:37][C:35]=3[N:36]=[C:31]([CH3:30])[N:32]=2)[CH2:45][CH2:44]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 1317297871-(2-Methylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine hcl-salt

Product 1

HCID 249364904-(2-Hydroxy-3-(1-(2-methylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)phenolYield 22%

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-(2-methylthieno[2,3-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 22% yield. Product was obtained by deprotection according to SP7 and purification by prep. HPLC (reversed phase) and prep. TLC (1 mm silica gel, PE/CH2Cl2/MeOH 3:7:1.5) with 25% 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-0fac9fc95e9b4009af2f76ce1059bf82
Source dataset
uspto-grants-2012_06
Patent number
US08207174B2

Reaction notes

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