1-(5-Phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine → 3-(2-Hydroxy-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)phenol

HRID 221646Notes

Reaction equation

HRID 221646 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.[C:21]1([C:27]2[C:35]3[C:34]([N:36]4[CH2:41][CH2:40][CH:39]([NH2:42])[CH2:38][CH2:37]4)=[N:33][CH:32]=[N:31][C:30]=3[S:29][CH:28]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CC(O)C.CS(C)=O>[OH:19][CH:18]([CH2:20][NH:42][CH:39]1[CH2:40][CH2:41][N:36]([C:34]2[C:35]3[C:27]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:28][S:29][C:30]=3[N:31]=[CH:32][N:33]=2)[CH2:37][CH2:38]1)[CH2:17][O:16][C:12]1[CH:11]=[C:10]([OH:9])[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 690415621-(5-Phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amineHCID 866235993-(Oxiran-2-ylmethoxy)phenyl benzoate

Product 1

HCID 249368813-(2-Hydroxy-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)phenolYield 20%

Reagents, catalysts & solvents 1

HCID 87082799iPrOH DMSOSolvent

Procedure

Synthesis followed SP6 (iPrOH:DMSO 3:1, 24 h), using 150 μmol 3-(oxiran-2-ylmethoxy)phenyl benzoate and 1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine. The benzoic acid moiety was already lost during purification by prep. TLC (1 mm silica gel, PE/CH2Cl2/MeOH 4:6:1) and subsequent prep. HPLC (reversed phase) to give the title compound with 20% yield.

Workup

  1. customSynthesis
  2. customThe benzoic acid moiety was already lost during purification by prep

Sources & evidence

ORD record
ord-9eba15d297154542b6801b448c926403
Source dataset
uspto-grants-2012_06
Patent number
US08207174B2

Reaction notes

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