2,4,5-Trichloropyrimidine → HCID 86674892, compound

HRID 1184705Notes

Reaction equation

HRID 1184705 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[CH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:16][C:17]1[N:22]=[C:21](Cl)[C:20]([Cl:24])=[CH:19][N:18]=1>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[C:15][C:19]2[C:20]([Cl:24])=[CH:21][N:22]=[C:17]([Cl:16])[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 2372592,4,5-TrichloropyrimidineHCID 15550481tert-Butyl 4-ethynylpiperidine-1-carboxylate

Product 1

HCID 86674892HCID 86674892, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-ethynyl-piperidine-1-carboxylic acid tert-butyl ester (1.73 g), 2,4,5-trichloro-pyrimidine (0.86 mL), Pd(PPh3)2Cl2 (105 mg), and copper iodide (29 mg) in triethylamine (15 mL) under an argon atmosphere is heated in a microwave oven at 100° C. for 40 min. The solvent is evaporated in vacuo and 1 N citric acid is added. The mixture is extracted with dichloromethane and the combined extracts are washed with water, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 85:15→80:20) to give the title compound. LC (method 7): tR=1.55 min; Mass spectrum (ESI+): m/z=356 [M+H]+.

Workup

  1. customThe solvent is evaporated in vacuo and 1 N citric acid
  2. additionis added
  3. extractionThe mixture is extracted with dichloromethane
  4. washthe combined extracts are washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 85:15→80:20)

Sources & evidence

ORD record
ord-4eb16884984d4102a6aa6aec19771baf
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

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