1-(5-Phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine → HCID 69045288, compound

HRID 221656Notes

Reaction equation

HRID 221656 reaction equation
[F:1][C:2]1[C:12]([F:13])=[C:11]([O:14][CH3:15])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH:6]1[CH2:8][O:7]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>>[F:1][C:2]1[C:12]([F:13])=[C:11]([O:14][CH3:15])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH:6]([OH:7])[CH2:8][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

Participants

3

Reactant 2

HCID 690415621-(5-Phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amineHCID 86623602HCID 86623602, compound

Product 1

HCID 69045288HCID 69045288, compoundYield 49%

Procedure

Synthesis followed SP6 (3 h), using 430 μmol 2-((2,3-difluoro-4-methoxyphenoxy)methyl)oxirane and 1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine to give O-methylated intermediate 1-(2,3-difluoro-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 49% yield. Product was obtained by O-demethylation according to SP12 (3 h) with 58% yield (LCMS: detected [M+1]=513.2).

Workup

  1. customSynthesis
  2. customSP6 (3 h)

Sources & evidence

ORD record
ord-6c7bed9698bc495288b53bd9630faebb
Source dataset
uspto-grants-2012_06
Patent number
US08207174B2

Reaction notes

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