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

HRID 221648Notes

Reaction equation

HRID 221648 reaction equation
COC[O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:15][CH2:16][CH:17]2[CH2:19][O:18]2)[CH:6]=1.[C:20]1([C:26]2[C:34]3[C:33]([N:35]4[CH2:40][CH2:39][CH:38]([NH2:41])[CH2:37][CH2:36]4)=[N:32][CH:31]=[N:30][C:29]=3[S:28][CH:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[OH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:15][CH2:16][CH:17]([OH:18])[CH2:19][NH:41][CH:38]2[CH2:39][CH2:40][N:35]([C:33]3[C:34]4[C:26]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[CH:27][S:28][C:29]=4[N:30]=[CH:31][N:32]=3)[CH2:36][CH2:37]2)[CH:6]=1

Participants

3

Reactant 2

HCID 690415621-(5-Phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amineHCID 86623601Methyl 4-(methoxymethoxy)-2-(oxiran-2-ylmethoxy)benzoate

Product 1

HCID 24937270Methyl 4-hydroxy-2-(2-hydroxy-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)benzoateYield 51%

Procedure

Synthesis followed SP6 (3 h), using 300 μmol methyl 4-(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 (1 mm silica gel, PE/CH2Cl2/MeOH 10:6:1) with 51% 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 6:4:1) and subsequent prep. HPLC (reversed phase).

Workup

  1. customSynthesis
  2. customSP6 (3 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-d7709961519343ceb5f1b54d85b78754
Source dataset
uspto-grants-2012_06
Patent number
US08207174B2

Reaction notes

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