Diisopropylethylamine → 1-(3-(Hydroxymethyl)phenoxy)-3-(1-(2-methylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propan-2-ol

HRID 221651Notes

Reaction equation

HRID 221651 reaction equation
CCN(C(C)C)C(C)C.[O:10]1[CH2:12][CH:11]1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][OH:22])[CH:18]=[CH:19][CH:20]=1.Cl.[CH3:24][C:25]1[N:26]=[C:27]([N:34]2[CH2:39][CH2:38][CH:37]([NH2:40])[CH2:36][CH2:35]2)[C:28]2[CH:33]=[CH:32][S:31][C:29]=2[N:30]=1>CC(O)C.CS(C)=O>[OH:22][CH2:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[O:14][CH2:13][CH:11]([OH:10])[CH2:12][NH:40][CH:37]1[CH2:36][CH2:35][N:34]([C:27]2[C:28]3[CH:33]=[CH:32][S:31][C:29]=3[N:30]=[C:25]([CH3:24])[N:26]=2)[CH2:39][CH2:38]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 19385010(3-(Oxiran-2-ylmethoxy)phenyl)methanolHCID 1317297871-(2-Methylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine hcl-salt

Product 1

HCID 249372661-(3-(Hydroxymethyl)phenoxy)-3-(1-(2-methylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propan-2-olYield 20%

Reagents, catalysts & solvents 1

HCID 87082799iPrOH DMSOSolvent

Procedure

Synthesis followed SP6 (iPrOH:DMSO 1:1, 1.2 eq. DIEA, 120° C., 90 h), using 150 μmol (3-(oxiran-2-ylmethoxy)phenyl)methanol and 1-(2-methylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine HCl-salt to give the title compound with 20% 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-e2e09774125c4e959966fcd5b9be5075
Source dataset
uspto-grants-2012_06
Patent number
US08207174B2

Reaction notes

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