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

HRID 221636Notes

Reaction equation

HRID 221636 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.[C:20]1([C:26]2[C:34]3[C:33]([N:35]4[CH2:40][CH2:39][CH:38]([NH2:41])[CH2:37][CH2:36]4)=[N:32][CH:31]=[N:30][C:29]=3[S:28][CH:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[OH:16][CH:15]([CH2:17][NH:41][CH:38]1[CH2:39][CH2:40][N:35]([C:33]2[C:34]3[C:26]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:27][S:28][C:29]=3[N:30]=[CH:31][N:32]=2)[CH2:36][CH2:37]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 690415621-(5-Phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine

Product 1

HCID 249364894-(2-Hydroxy-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)phenolYield 21%

Procedure

Synthesis followed SP6 (3 h), using 220 μmol tert-butyldimethyl(4-(oxiran-2-ylmethoxy)phenoxy)silane and 1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine to give O-silylated intermediate upon purification by prep. HPLC (reversed phase) with 21% yield. Product was obtained by deprotection according to SP7 and purification by prep. HPLC (reversed phase) with 70% yield.

Workup

  1. customSynthesis
  2. customSP6 (3 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-db3e060e84df466588edd70edd129e8c
Source dataset
uspto-grants-2012_06
Patent number
US08207174B2

Reaction notes

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