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

HRID 221647Notes

Reaction equation

HRID 221647 reaction equation
COC[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:16][CH2:17][CH:18]2[CH2:20][O:19]2)=[C:9]([CH:15]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11].[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>>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([O:16][CH2:17][CH:18]([OH:19])[CH2:20][NH:42][CH:39]2[CH2:40][CH2:41][N:36]([C:34]3[C:35]4[C:27]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)=[CH:28][S:29][C:30]=4[N:31]=[CH:32][N:33]=3)[CH2:37][CH2:38]2)=[C:9]([CH:15]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

3

Reactant 2

HCID 690415621-(5-Phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amineHCID 86623600Ethyl 5-(methoxymethoxy)-2-(oxiran-2-ylmethoxy)benzoate

Product 1

HCID 24937015Ethyl 5-hydroxy-2-(2-hydroxy-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)benzoateYield 48%

Procedure

Synthesis followed SP6 (6 h), using 250 μmol ethyl 5-(methoxymethoxy)-2-(oxiran-2-ylmethoxy)benzoate and 1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine to give MOM intermediate upon purification by prep. TLC (2 mm silica gel, PE/CH2Cl2/MeOH 4:6:1) with 48% yield. Product was obtained by MOM-removal according to SP8 with 32% yield upon purification by prep. TLC (1 mm silica gel, PE/CH2Cl2/MeOH 2:5:1).

Workup

  1. customSynthesis
  2. customSP6 (6 h)
  3. customto give MOM intermediate
  4. customupon purification by prep
  5. customProduct was obtained by MOM-removal
  6. customaccording to SP8 with 32% yield upon purification by prep

Sources & evidence

ORD record
ord-4bc4010c07b5404eb69b17823446252f
Source dataset
uspto-grants-2012_06
Patent number
US08207174B2

Reaction notes

Loading…