Pyridine → HCID 89579977, compound

HRID 928594Notes

Reaction equation

HRID 928594 reaction equation
[C:1]1([C:7]2[C:15]3[C:14](=O)[NH:13][C:12]([C:17]([F:20])([F:19])[F:18])=[N:11][C:10]=3[S:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[N:42]1([CH2:47][CH2:48][O:49][CH2:50][CH:51]2[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]2)[CH2:46][CH2:45][CH2:44][CH2:43]1>ClCCl>[C:1]1([C:7]2[C:15]3[C:14]([N:54]4[CH2:55][CH2:56][CH:51]([CH2:50][O:49][CH2:48][CH2:47][N:42]5[CH2:46][CH2:45][CH2:44][CH2:43]5)[CH2:52][CH2:53]4)=[N:13][C:12]([C:17]([F:20])([F:19])[F:18])=[N:11][C:10]=3[S:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 623388724-(2-Pyrrolidin-1-ylethoxymethyl)piperidineHCID 67382085HCID 67382085, compound

Product 1

HCID 89579977HCID 89579977, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Phenyl-2-(trifluoromethyl)thieno[2,3-d]pyrimidin-4-one (0.20 g, 0.67 mmol) was stirred in dichloromethane (5 mL) at 0° C. Pyridine (0.11 mL, 1.3 mmol) was added, followed by trifluoromethanesulfonic anhydride (0.14 mL, 0.81 mmol) and stirring continued for 30 mins and the mixture allowed to warm to room temperature. 4-(2-Pyrrolidin-1-ylethoxymethyl)piperidine (0.29 g, 1.3 mmol) was added and the reaction stirred for 1 hour at room temperature. The reaction mixture was diluted with DCM (20 mL), washed with water (20 mL), dried over Na2SO4 and concentrated at reduced pressure. The resulting residue was purified by flash chromatography, eluting with a gradient of petroleum ether to 50/50 petroleum ether/ethyl acetate to afford 5-phenyl-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]-2-(trifluoromethyl)thieno[2,3-d]pyrimidine (0.16 g). LCMS: purity 98%, RT=4.28 min, M+1=491.2

Workup

  1. stirringthe reaction stirred for 1 hour at room temperature
  2. washwashed with water (20 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated at reduced pressure
  5. customThe resulting residue was purified by flash chromatography
  6. washeluting with a gradient of petroleum ether to 50/50 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-46fb52dda6eb469bbf794b93c38e2213
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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