(3-(Oxiran-2-ylmethoxy)phenyl)methanol → 1-(1-(5-(4-Fluorophenyl)thieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)-3-(3-(hydroxymethyl)phenoxy)propan-2-ol

HRID 221653Notes

Reaction equation

HRID 221653 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][OH:13])[CH:9]=[CH:10][CH:11]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:29]3[C:28]([N:30]4[CH2:35][CH2:34][CH:33]([NH2:36])[CH2:32][CH2:31]4)=[N:27][CH:26]=[N:25][C:24]=3[S:23][CH:22]=2)=[CH:17][CH:16]=1>CC(O)C.CS(C)=O>[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:29]3[C:28]([N:30]4[CH2:35][CH2:34][CH:33]([NH:36][CH2:3][CH:2]([OH:1])[CH2:4][O:5][C:6]5[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][OH:13])[CH:7]=5)[CH2:32][CH2:31]4)=[N:27][CH:26]=[N:25][C:24]=3[S:23][CH:22]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 19385010(3-(Oxiran-2-ylmethoxy)phenyl)methanolHCID 690409951-(5-(4-Fluorophenyl)thieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine

Product 1

HCID 249371421-(1-(5-(4-Fluorophenyl)thieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)-3-(3-(hydroxymethyl)phenoxy)propan-2-olYield 35%

Reagents, catalysts & solvents 1

HCID 87082799iPrOH DMSOSolvent

Procedure

Synthesis followed SP6 (iPrOH:DMSO 1:1, 14 h), using 150 μmol (3-(oxiran-2-ylmethoxy)phenyl)methanol and 1-(5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine to give the title compound with 35% yield upon purification by prep. HPLC (reversed phase).

Workup

  1. customSynthesis

Sources & evidence

ORD record
ord-a53378432fe14bee9ba5dce6c5f76a0d
Source dataset
uspto-grants-2012_06
Patent number
US08207174B2

Reaction notes

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