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

HRID 221650Notes

Reaction equation

HRID 221650 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.[CH3:14][C:15]1[C:23]2[C:22]([N:24]3[CH2:29][CH2:28][CH:27]([NH2:30])[CH2:26][CH2:25]3)=[N:21][CH:20]=[N:19][C:18]=2[S:17][CH:16]=1>CC(O)C.CS(C)=O>[OH:13][CH2:12][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[O:5][CH2:4][CH:2]([OH:1])[CH2:3][NH:30][CH:27]1[CH2:26][CH2:25][N:24]([C:22]2[C:23]3[C:15]([CH3:14])=[CH:16][S:17][C:18]=3[N:19]=[CH:20][N:21]=2)[CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 19385010(3-(Oxiran-2-ylmethoxy)phenyl)methanolHCID 690423951-(5-Methylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine

Product 1

HCID 249372681-(3-(Hydroxymethyl)phenoxy)-3-(1-(5-methylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propan-2-olYield 26%

Reagents, catalysts & solvents 1

HCID 87082799iPrOH DMSOSolvent

Procedure

Synthesis followed SP6 (iPrOH:DMSO 1:1, 30 h at 80° C. and 20 h at 100° C.), using 220 μmol (3-(oxiran-2-ylmethoxy)phenyl)methanol and 1-(5-methylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine to give the title compound with 26% yield upon purification by prep. HPLC (reversed phase) and subsequent by prep. TLC (1 mm silica gel, PE/CH2Cl2/MeOH 4:6:1).

Workup

  1. customSynthesis

Sources & evidence

ORD record
ord-15d2633c0ffc4ca48b566228be688967
Source dataset
uspto-grants-2012_06
Patent number
US08207174B2

Reaction notes

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