1-(5-Phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine → 1-(2-Fluoro-4-methoxyphenoxy)-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propan-2-ol

HRID 221657Notes

Reaction equation

HRID 221657 reaction equation
[F:1][C:2]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH:6]1[CH2:8][O:7]1.[C:15]1([C:21]2[C:29]3[C:28]([N:30]4[CH2:35][CH2:34][CH:33]([NH2:36])[CH2:32][CH2:31]4)=[N:27][CH:26]=[N:25][C:24]=3[S:23][CH:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[F:1][C:2]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH:6]([OH:7])[CH2:8][NH:36][CH:33]1[CH2:34][CH2:35][N:30]([C:28]2[C:29]3[C:21]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[CH:22][S:23][C:24]=3[N:25]=[CH:26][N:27]=2)[CH2:31][CH2:32]1

Participants

3

Reactant 2

HCID 690415621-(5-Phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amineHCID 866236032-((2-Fluoro-4-methoxyphenoxy)methyl)oxirane

Product 1

HCID 690430541-(2-Fluoro-4-methoxyphenoxy)-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propan-2-olYield 40%

Procedure

Synthesis followed SP6 (3 h), using 300 μmol 2-((2-fluoro-4-methoxyphenoxy)methyl)oxirane and 1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine to give O-methylated intermediate 1-(2-fluoro-4-methoxyphenoxy)-3-(1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)propan-2-ol upon purification by prep. TLC (1 mm silica gel, PE/CH2Cl2/MeOH 4:6:1) with 40% yield. Product was obtained by O-demethylation according to SP12 (1 h) with 37% yield (LCMS: detected [M+1]=495.2).

Workup

  1. customSynthesis
  2. customSP6 (3 h)

Sources & evidence

ORD record
ord-c99dd9b0a37b4e77b0b1d15690e04731
Source dataset
uspto-grants-2012_06
Patent number
US08207174B2

Reaction notes

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