2-{[4-(Hydroxymethyl)phenoxy]methyl}oxirane → 1-(4-(Hydroxymethyl)phenoxy)-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propan-2-ol

HRID 221654Notes

Reaction equation

HRID 221654 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][CH:7]=1.[C:14]1([C:20]2[C:28]3[C:27]([N:29]4[CH2:34][CH2:33][CH:32]([NH2:35])[CH2:31][CH2:30]4)=[N:26][CH:25]=[N:24][C:23]=3[S:22][CH:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[OH:13][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH:2]([OH:1])[CH2:3][NH:35][CH:32]2[CH2:33][CH2:34][N:29]([C:27]3[C:28]4[C:20]([C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)=[CH:21][S:22][C:23]=4[N:24]=[CH:25][N:26]=3)[CH2:30][CH2:31]2)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 248237062-{[4-(Hydroxymethyl)phenoxy]methyl}oxiraneHCID 690415621-(5-Phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine

Product 1

HCID 249371401-(4-(Hydroxymethyl)phenoxy)-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propan-2-olYield 19%

Procedure

Synthesis followed SP6 (4 h), using 120 μmol (4-(oxiran-2-ylmethoxy)phenyl)methanol and 1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine to give the title compound with 19% yield upon purification by prep. HPLC (reversed phase).

Workup

  1. customSynthesis
  2. customSP6 (4 h)

Sources & evidence

ORD record
ord-72ca669110b54433a8ec81f56afbc0a0
Source dataset
uspto-grants-2012_06
Patent number
US08207174B2

Reaction notes

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