Dimethylformamide → 2-Chloro-6-methyl-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 2189307Notes

Reaction equation

HRID 2189307 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:5]([C:14]#[C:15][CH3:16])=[CH:4][N:3]=1.CN(C=O)C>CCOC(C)=O.[Cu]I>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:14]=[C:15]([CH3:16])[N:8]([CH:9]([CH2:10][CH3:11])[CH2:12][CH3:13])[C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 580159552-chloro-N-(pentan-3-yl)-5-(prop-1-ynyl)pyrimidin-4-amine

Product 1

HCID 580158152-Chloro-6-methyl-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidineYield 19.7%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

To a microwave vial are added (2-chloro-5-prop-1-ynyl-pyrimidin-4-yl)-(1-ethyl-propyl)-amine (0.22 g, 0.92 mmol), anhydrous DMF (3 mL), and CuI (53 mg, 0.27 mmol). The reaction is heated at 160° C. for 1 h by employing microwave. The reaction mixture is diluted with EtOAc, washed with NaHCO3 aqueous solution and water, dried over Na2SO4, and concentrated in vacuo. Purification with column chromatography (SiO2, EtOAC/hexane 1:4) gives 43 mg of 2-chloro-7-(1-ethyl-propyl)-6-methyl-7H-pyrrolo[2,3-d]pyrimidine.

Workup

  1. washwashed with NaHCO3 aqueous solution and water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customPurification with column chromatography (SiO2, EtOAC/hexane 1:4)

Sources & evidence

ORD record
ord-17404167c06c41fdb9576d2d142dc67f
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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