Tert-butyldimethyl(4-(oxiran-2-ylmethoxy)phenoxy)silane → 4-(2-Hydroxy-3-(1-(5-methyl-6-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)phenol

HRID 221641Notes

Reaction equation

HRID 221641 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.[CH3:20][C:21]1[C:29]2[C:28]([N:30]3[CH2:35][CH2:34][CH:33]([NH2:36])[CH2:32][CH2:31]3)=[N:27][CH:26]=[N:25][C:24]=2[S:23][C:22]=1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[OH:16][CH:15]([CH2:17][NH:36][CH:33]1[CH2:34][CH2:35][N:30]([C:28]2[C:29]3[C:21]([CH3:20])=[C:22]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[S:23][C:24]=3[N:25]=[CH:26][N:27]=2)[CH2:31][CH2:32]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 690431471-(5-Methyl-6-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine

Product 1

HCID 249373904-(2-Hydroxy-3-(1-(5-methyl-6-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)phenolYield 17%

Procedure

Synthesis followed SP6 (3 h), using 150 μmol tert-butyldimethyl(4-(oxiran-2-ylmethoxy)phenoxy)silane and 1-(5-methyl-6-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine to give O-silylated intermediate upon purification by prep. HPLC (reversed phase) with 17% yield. Product was obtained by deprotection according to SP7 and purification by prep. HPLC (reversed phase) with 14% 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-d51d8edcf9b346bca918318be10d59c4
Source dataset
uspto-grants-2012_06
Patent number
US08207174B2

Reaction notes

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