4-Pyrimidinamine, 2,6-dichloro- → 2-(2-Cyclopentylethynyl)-6-chloropyrimidin-4-amine

HRID 1971037Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[CH:10]1([C:15]#[CH:16])[CH2:14][CH2:13][CH2:12][CH2:11]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu](I)I.C1COCC1.C(N(CC)CC)C>[CH:10]1([C:15]#[C:16][C:2]2[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:9])[N:3]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

Conditions

Temperature: 100 °C

Procedure

2,6-Dichloropyrimidin-4-amine (0.2 g, 1.22 mmol), tetrakis(triphenylphosphine)palladium(0) (42 mg, 0.043 mmol) and copper iodide (14 mg, 0.07 mmol) were introduced in a flask. A mixture of THF-triethylamine 2:3 (5 mL) was added and the system was inertized 3 times with vacuum/argon cycles. Finally, cyclopentyl acetylene (0.16 mL, 1.34 mmol) was added and the resulting mixture was heated at 100° C. overnight. The reaction crude was cooled at room temperature and filtered over Celite®. The solvent was evaporated to dryness and the residue was purified by chromatography over silica gel using mixtures of hexane/EtOAc of increasing polarity as eluent, providing 0.15 g of the title compound, impurified with its regioisomer.

Workup

additionwas added
customThe reaction crude
temperaturewas cooled at room temperature
filtrationfiltered over Celite®
customThe solvent was evaporated to dryness
customthe residue was purified by chromatography over silica gel using mixtures of hexane/EtOAc
temperatureof increasing polarity as eluent

Sources & evidence

ORD record: ord-5a6f45234eeb49a497b9498398ba525c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431580B2

Reaction notes

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