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

HRID 2189282Notes

Reaction equation

HRID 2189282 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

In a microwave vial is 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 hr by employing microwave. The reaction mixture is diluted with EtOAc, washed with sat. NaHCO3 aqueous solution and water, dried over Na2SO4, and concentrated in vacuo. Purification with column chromatography (SiO2, 1:4 EtOAC/Hexane) gives 43 mg of the desired product.

Workup

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

Sources & evidence

ORD record
ord-15d4e1ca3c834d57913ea4454efcc380
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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