1-(4,6-Dimethylpyrimidin-2-yl)piperidin-4-amine → 1-(1-(4,6-Dimethylpyrimidin-2-yl)piperidin-4-ylamino)-3-(3-(hydroxymethyl)phenoxy)propan-2-ol

HRID 221659Notes

Reaction equation

HRID 221659 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[CH:20]=[C:19]([CH3:21])[N:18]=[C:17]([N:22]2[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]2)[N:16]=1>CC(O)C.CS(C)=O>[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[N:18]=[C:17]([N:22]2[CH2:23][CH2:24][CH:25]([NH:28][CH2:3][CH:2]([OH:1])[CH2:4][O:5][C:6]3[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][OH:13])[CH:7]=3)[CH2:26][CH2:27]2)[N:16]=1

Participants

4

Reactant 2

HCID 47782891-(4,6-Dimethylpyrimidin-2-yl)piperidin-4-amineHCID 19385010(3-(Oxiran-2-ylmethoxy)phenyl)methanol

Product 1

HCID 598198971-(1-(4,6-Dimethylpyrimidin-2-yl)piperidin-4-ylamino)-3-(3-(hydroxymethyl)phenoxy)propan-2-olYield 9%

Reagents, catalysts & solvents 1

HCID 87082799iPrOH DMSOSolvent

Procedure

Synthesis followed SP6 (iPrOH:DMSO 1:1, 120° C., 24 h), using 200 μmol (3-(oxiran-2-ylmethoxy)phenyl)methanol and 1-(4,6-dimethylpyrimidin-2-yl)piperidin-4-amine to give the title compound with 9% yield upon purification by prep. HPLC (reversed phase) and subsequent by prep. TLC (1 mm silica gel, PE/CH2Cl2/MeOH 4:6:1) (LCMS: detected [M+1]=387.2).

Workup

  1. customSynthesis

Sources & evidence

ORD record
ord-f3d349709dbd458a912401bde71276c2
Source dataset
uspto-grants-2012_06
Patent number
US08207174B2

Reaction notes

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