Triethylamine → [1-(2-Chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-4-piperidyl]methanol

HRID 928558Notes

Reaction equation

HRID 928558 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[Cl:9][C:10]1[N:11]=[C:12](Cl)[C:13]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][S:16][C:14]=2[N:15]=1.C(N(CC)CC)C>C(O)C>[Cl:9][C:10]1[N:11]=[C:12]([N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]2)[C:13]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][S:16][C:14]=2[N:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4207714-PiperidinemethanolHCID 127242282,4-Dichloro-5-phenylthieno(2,3-d)pyrimidine

Product 1

HCID 89579549[1-(2-Chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-4-piperidyl]methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

4-Piperidinemethanol (987 mg, 8.57 mmol) was added to a stirred suspension of 2,4-dichloro-5-phenyl-thieno[2,3-d]pyrimidine (2 g, 7.14 mmol) and triethylamine (2.18 ml, 15.7 mmol) in dry ethanol (ml) at room temperature. Reaction was warmed to 40° C. and the resulting solution stirred for ˜2 h. Reaction was allowed to cool to room temperature and poured onto ice/water (50 ml). The resulting suspension was filtered and the solid dried in a vacuum oven at 40° C. The desired compound was obtained as a pale yellow solid (2.4 g, 93%). LCMS: (M+1) 360, RT=4.69 min.

Workup

  1. customReaction
  2. customReaction
  3. temperatureto cool to room temperature
  4. additionpoured onto ice/water (50 ml)
  5. filtrationThe resulting suspension was filtered
  6. customthe solid dried in a vacuum oven at 40° C

Sources & evidence

ORD record
ord-6253a31637214510b48cfecde35bbf41
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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