N-Piperidinoethanol → HCID 89579413, compound

HRID 928576Notes

Reaction equation

HRID 928576 reaction equation
[H-].[Na+].[N:3]1([CH2:9][CH2:10][OH:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl[C:13]1[C:14]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][S:19][C:15]=2[N:16]=[CH:17][N:18]=1>C1COCC1.O>[C:22]1([C:21]2[C:14]3[C:13]([O:11][CH2:10][CH2:9][N:3]4[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]4)=[N:18][CH:17]=[N:16][C:15]=3[S:19][CH:20]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 18232N-PiperidinoethanolHCID 24758Sodium hydrideHCID 7087304-Chloro-5-phenylthieno[2,3-d]pyrimidine

Product 1

HCID 89579413HCID 89579413, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (8 mg, 0.16 mmol) was suspended in dry THF (0.5 mL). To this was added 2-(1-piperidyl)ethanol (16 μL, 0.12 mmol) and the reaction stirred for 10 min until effervescence had ceased. Then 4-chloro-5-phenyl-thieno[2,3-d]pyrimidine (20 mg, 0.08 mmol) in dry THF (0.5 mL) was added and the reaction left to stir at room temperature for 72 hrs. The reaction mixture was diluted with water and extracted with DCM. The organic layers were concentrated and the residue purified by preparative TLC (eluent 10% MeOH in DCM) to give 5-phenyl-4-[2-(1-piperidyl)ethoxy]thieno[2,3-d]pyrimidine as a yellow oil (19.4 mg, 72%). LCMS RT=3.03 min. M+1=340.

Workup

  1. waitthe reaction left
  2. stirringto stir at room temperature for 72 hrs
  3. extractionextracted with DCM
  4. concentrationThe organic layers were concentrated
  5. customthe residue purified by preparative TLC (eluent 10% MeOH in DCM)

Sources & evidence

ORD record
ord-0649d3a11c2b49ebb79939da9e3a81d6
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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