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

HRID 221637Notes

Reaction equation

HRID 221637 reaction equation
COC[O:4][C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C@H:11]2[CH2:13][O:12]2)=[CH:7][CH:6]=1.[C:16]1([C:22]2[C:30]3[C:29]([N:31]4[CH2:36][CH2:35][CH:34]([NH2:37])[CH2:33][CH2:32]4)=[N:28][CH:27]=[N:26][C:25]=3[S:24][CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[OH:12][C@H:11]([CH2:13][NH:37][CH:34]1[CH2:35][CH2:36][N:31]([C:29]2[C:30]3[C:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:23][S:24][C:25]=3[N:26]=[CH:27][N:28]=2)[CH2:32][CH2:33]1)[CH2:10][O:9][C:8]1[CH:7]=[CH:6][C:5]([OH:4])=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 690415621-(5-Phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amineHCID 86623598(R)-2-((4-(methoxymethoxy)phenoxy)methyl)oxirane

Product 1

HCID 25001235(R)-4-(2-hydroxy-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propoxy)phenolYield 57%

Procedure

Synthesis followed SP6 (4 h), using 250 μmol (R)-2-((4-(methoxymethoxy)phenoxy)methyl)oxirane and 1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine to give O-MOM intermediate upon purification by prep. TLC (2 mm silica gel, PE/CH2Cl2/MeOH 4:6:1) with 57% yield. Product was obtained by MOM removal according to SP8 (1.5 eq. TosOH, 10 h) and purification by prep. TLC (1 mm silica gel, CH2Cl2/MeOH 90:10) with 55% yield.

Workup

  1. customSynthesis
  2. customSP6 (4 h)
  3. customto give O-MOM intermediate
  4. customupon purification by prep
  5. customProduct was obtained by MOM removal
  6. customaccording to SP8 (1.5 eq. TosOH, 10 h) and purification by prep

Sources & evidence

ORD record
ord-49cd62d50f9e4ea5a7e04bd296c2b218
Source dataset
uspto-grants-2012_06
Patent number
US08207174B2

Reaction notes

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