1-(4,6-Dimethylpyrimidin-2-yl)piperidin-4-amine → 3-(3-(1-(4,6-Dimethylpyrimidin-2-yl)piperidin-4-ylamino)-2-hydroxypropoxy)phenol

HRID 221658Notes

Reaction equation

HRID 221658 reaction equation
C([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH:18]2[CH2:20][O:19]2)[CH:11]=1)(=O)C1C=CC=CC=1.[CH3:21][C:22]1[CH:27]=[C:26]([CH3:28])[N:25]=[C:24]([N:29]2[CH2:34][CH2:33][CH:32]([NH2:35])[CH2:31][CH2:30]2)[N:23]=1.C1C=CC(=O)C(O)=C(C2C=NC=NC=2)C=1>CC(O)C.CS(C)=O>[CH3:21][C:22]1[CH:27]=[C:26]([CH3:28])[N:25]=[C:24]([N:29]2[CH2:30][CH2:31][CH:32]([NH:35][CH2:20][CH:18]([OH:19])[CH2:17][O:16][C:12]3[CH:11]=[C:10]([OH:9])[CH:15]=[CH:14][CH:13]=3)[CH2:33][CH2:34]2)[N:23]=1

Participants

5

Reactant 3

HCID 47782891-(4,6-Dimethylpyrimidin-2-yl)piperidin-4-amineHCID 107505172-Hydroxy-7-pyrimidin-5-yl-cyclohepta-2,4,6-trien-1-oneHCID 866235993-(Oxiran-2-ylmethoxy)phenyl benzoate

Product 1

HCID 598198963-(3-(1-(4,6-Dimethylpyrimidin-2-yl)piperidin-4-ylamino)-2-hydroxypropoxy)phenolYield 14%

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 benzoate and 1-(4,6-dimethylpyrimidin-2-yl)piperidin-4-amine to give O-benzoylated intermediate, which was directly treated according to SP10. Title product was obtained by purification by prep. HPLC (reversed phase) and prep. TLC (1 mm silica gel, PE/CH2Cl2/MeOH 4:6:1) with 14% yield (LCMS: detected [M+1]=373.2).

Workup

  1. customSynthesis
  2. customto give O-benzoylated intermediate, which
  3. additionwas directly treated

Sources & evidence

ORD record
ord-e835f9dbf68246c9b430c80fe043c6cb
Source dataset
uspto-grants-2012_06
Patent number
US08207174B2

Reaction notes

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